Tag: M.W=100-200

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of 1-(4-Methoxyphenyl)ethylamine

A slurry of sodium triacetoxyborohydride (4.54 Kg, 21.4 mol.) in dichloromethane (22 Liters) is treated with 6,7-dihydro-8(5/-/)-quinolinone (1.8 Kg, 12.3 mol.) followed by (1S)-1-[4-(methyloxy)phenyl]ethanamine (1.8 Kg, 11.9 mol).) and the reaction was allowed to stirr vigorously at 22 0C for 24 hrs. The reaction is quenched with 1 N NaOH (aprox 27 Liters) to achieve pH 8 in the aqueous layer. The phases were separated and the organic phase was treated with 1N sodium hydroxide ( aprox 3.5 Liters) to achieve pH 11 in the aqueous layer. The phases again separated. The dichloromethane solution was then concentrated to minimum volume and treated with heptane (18 Liters). The volume again concentrated to aprox 9 Liters. Precipitation occurred upon cooling to 22 0C. The suspension was further cooled to 00C. and filtered. Solids were dried at ambient temperature under vacuum with nitrogen to give (8S)-N-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-5,6,7,8-tetrahydro-8- quinolinamine. (2.18 Kg, 63%) 1H NMR (400 MHz, DMSO-D6) delta ppm 8.36 (m, 1 H) 7.44 (m, 1 H) 7.29 (m, 2 H) 7.15 (m, 1 H) 6.83 (m, 2 H) 4.00 (m, 1 H) 3.70 (s, 3 H) 3.59 – 3.64 (m, 1 H) 2.66 (m, 1 H) 2.64 (s, 1 H) 2.53 (s, 1 H) 1.76 (s, 1 H) 1.64 (s, 1 H) 1.50 (s, 1 H) 1.39 (s, 1 H) 1.24 (m, 3 H)

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/87549; (2007); A2;,
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Electric Literature of 39021-83-5,Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step 1 2,3-Dimethyl-5,6-dinitro-1,4-dimethoxybenzene A solution of 2,3-dimethyl-1,4-dimethoxybenzene (16.6 g; o.1 mol) in acetic acid (100 mL) was cooled in an ice bath, then conc. HNO3 (40 mL) was added dropwise over 15 minutes. After the addition, the reaction mixture was stirred at ambient temperature for 3 hours, then heated at 50 C. for 20 minutes. Solution was concentrated to 75 mL under vacuum, then poured into ice-H2O (350 mL). The yellow precipitate (8.1 g) was collected. Recrystallization from EtOH gave 5.4 g (18.5% yield) of 2,3-dimethyl-5,6-dinitro-1,4-dimethoxybenzene as a yellow solid, m.p. 147-150 C.

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US6444694; (2002); B1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

General procedure: To a mixture of alpha-azidoamide 16aa (34 mg, 0.20 mmol) and phenylacetylene (9a; 24 L,0.20 mmol) in t-BuOH/H2O (2 mL, 1:1) were added 0.5 M CuSO4 (0.020 mL, 0.010 mmol) and 1.0 M sodium ascorbate (0.020 mL, 0.020 mmol). The reaction mixture was stirred at room temperature for 1 day, and then the resulting reaction mixture was filtered. The separated solid was washed with H2O and hexanes, and triturated with hexane/EtOAc (10:1) to give the 1-morpholino-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (2aaa; 52 mg, 96%) as a white solid

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Lee, Doohyun; Kim, Daehun; Lee, Seungyeon; Kim, Taegeum; Kim, Joobin; Kim, Sohee; Liu, Kwang-Hyeon; Lee, Sangkyu; Bae, Jong-Sup; Song, Kyung-Sik; Cho, Chang-Woo; Son, Youn Kyung; Baek, Dong Jae; Lee, Taeho; Molecules; vol. 20; 11; (2015); p. 19984 – 20013;,
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Electric Literature of 38336-04-8,Some common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, molecular formula is C9H13NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (9.8 g, 25 mmol) in dichloromethane (100 mL) was added 128 (4 g, 26 mmol) at 0 C. After stirred for 2 hours, trifluoro acetic acid (15.4 g, 159 mmol) was added. The resulting solution was stirred for 12 hours at room temperature, then quenched with ice- water (200 mL) and neutralized by the addition ofNaHCC”3 (26 g, 318 mmol). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×100 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to give a residue, which was purified by silica gel column, eluted with 10 % – 50 % ethyl acetate in petroleum ether to afford 129 as a white syrup (9.8 g, 77 %). (ES, m/z) [M+H]+ 481.0; 1H NMR (300 MHz, CDC13) delta 7.31 – 7.38 (m, 5H), 6.24 (d, / = 6.3 Hz, 1H), 5.41 – 5.43 (m, 1H), 4.94 – 4.98 (m, 1H), 4.55 (s, 2H), 4.34 – 4.37 (m, 1H), 4.14 – 4.16 (m, 3H), 3.83 – 3.87 (m, 1H), 3.64 (t, / = 5.4 Hz, 2H), 3.53 (t, / = 5.1 Hz, 2H), 2.12 (s, 3H), 2.10 (s, 3H), 2.09 (s, 3H).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
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Application of 60792-79-2,Some common heterocyclic compound, 60792-79-2, name is 2,2′-Oxybis(ethylamine) dihydrochloride, molecular formula is C4H14Cl2N2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Example 7 Preparation of 5-((2-(2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethoxy)ethyl)carbamoyl)-2-methylpyrazine 1-oxide (I-4) In a typical run, sodium hydroxide (400 mg, 10 mmol) was dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) was added. The resulting reaction mixture was stirred at room temperature for 30 min A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) was then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture was stirred at room temperature for 18 h. It was then concentrated under reduced pressure. The resulting residue was taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture was filtered and the filtrate was concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate (850 mg, 74%).

The synthetic route of 60792-79-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Milne, Jill C.; Jirousek, Michael R.; Bemis, Jean E.; Vu, Chi B.; US2011/82156; (2011); A1;,
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Related Products of 7664-66-6, A common heterocyclic compound, 7664-66-6, name is 4-Isopropoxyaniline, molecular formula is C9H13NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of compound Al (0.5 g, 065 mmol) in toluene (10 rnL) and 4- Isopropoxyaniline (202 mg, 134 mmol) was added Ti(O-iPr)4 (190 mg, 0.66 rnmol). Themixture was stirred at 120 C overnight. The mixture was quenched with H20 (50 mL) and extracted with DCM (20 mE x 3). The combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by silica gel column chromatography (DCM/MeOH == 15/1) to afford the crude products 304 and 30-2 (140 rng) as a brown solid .LC-MS: rnz 899.2 [M+H]?. To a solution of compounds 304 and 30-2 (137 mg. 015 rnmoi) in DCM (5 mE) was added DAST (24.5 rng, 0.15 mrnoi) at -78 C underN2. After stirred at -78 C for I Ii, the mixture was quenched with aqueous NaHCO3 and H20 and then extracted with DCM (30 mL x 3). i1e combined organic layer was dried over potassium carbonate, filtered and concentrated. The residue was purified by prep-HPLC to afford compound 30 (19 mg, yield14%) as yellow solid. Partial ?H NMR (CDCi3, 400 MHz): 6.93 (d, J::: Hz, 2H), 6.78-6.75 (m, 3H), 4.88 (s, 1H), 4.71-4.66 (in, 1H), 4.46-4.33 (rn, 2H), 4,32-4.29 (m, IH), 3.66-3.63 (m, 1H). 3.29-3.26 (m, 2H), 3.13-3.09 (in. 2H), 3.56-2.33 (rn, 3H); EC-MS: m/z 81.2[M+l-[[5.

The synthetic route of 7664-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AGRIMETIS, LLC; CALABRESE, Andrew; (110 pag.)WO2018/132288; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 41406-00-2, name is 3-Isopropoxyaniline, belongs to ethers-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 41406-00-2, Safety of 3-Isopropoxyaniline

To a stirred solution of 2,6,6-trimethylcyclohex-l-enecarbaldehyde (99.5 mg, 0.66 mmol) in methanol (2 mL) ) was added 3-isopropoxyaniline (99.5 mg, 0.66 mmol) followed by acetic acid (0.1 mL), and sodium cyanoborohydride (124.0 mg, 1.97 mmol). The reaction was stirred at room temperature for 2 hours. The reaction was quenched by addition of saturated aqueous ammonium chloride (5 mL) and the organic volatiles were evaporated under reduced pressure. The resulting mixture was diluted with ethyl acetate (30 mL) and the organic phase was washed with water (20 mL), saturated aqueous sodium bicarbonate (20 mL) and brine (20 mL), dried over anhydrous sodum sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 90/1 ) to give the title compound as a colorless oil (137 mg, Yield: 72%). Rf = 0.6 (20:1 petroleum ether/ethyl acetate); H NMR (400 MHz, CDCI3) delta 7.05 (t, J = 8.0 Hz, 1 H), 6.24-6.18 (m, 2 H), 6.15-6.14 (m, 1 H), 4.56-4.50 (m, 1 H), 3.55 (s, 2 H), 3.30 (bs, 1 H), 1.97 (t, J = 6.2 Hz, 2 H), 1.66 (s, 3 H), 1.66-1.59 (m, 2 H), 1.50-1.43 (m, 2 H), 1.33 (d, J = 6.0 Hz, 6 H), .02 (s, 6 H) ppm; Mass spectrum (ESI +ve) m/z 288 (M + H+).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; BIKAM PHARMACEUTICALS, INC.; QUACH, Tan; BERMAN, Judd; GARVEY, David, S.; WO2013/81642; (2013); A1;,
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Application of 437-82-1,Some common heterocyclic compound, 437-82-1, name is 2,6-Difluoroanisole, molecular formula is C7H6F2O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The 2,6-difluoroanisole (4.00 ml, 33 . 9mmol) and sodium iodide (15.0g, 100mmol) dissolved in acetonitrile (50 ml) , trimethylchlorosilane (8.80 ml, 102mmol) is also added and heated to 100 C for 5 hours. Cooling to room temperature, reducing pressure and evaporating solvent, adding water (40 ml), dichloromethane is used for (30 ml × 3) extraction. Combined with the phase, with water (40 ml), saturated salt water (40 ml) washing, dry anhydrous sodium sulfate. Filtering, evaporating solvent under reduced pressure, the crude product purification column chromatography (petroleum ether/ethyl acetate (v/v)=6/1), to get the yellow oil (2.2g, 50%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Difluoroanisole, its application will become more common.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Zhuo, Yinglin; Wang, Xiaojun; Zhang, Yingjun; Wen, Liang; Wu, Shoutao; Yuan, Xiaofeng; (87 pag.)CN105384687; (2016); A;,
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Related Products of 3616-56-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis Example B13Synthesis of 3-bromo-12H-benzofuranyl[3,2-a]carbazole (compound 13)Under nitrogen, compound 12 (3.2 g, 1 eq) is initially charged and dissolved with acetic acid (30 ml) while heating to reflux.Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 21.9 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 48 h.The mixture is cooled to room temperature and diluted with methylene chloride.Washed in a separating funnel with distilled water and then with saturated NaCl solution.The organic phase is dried with sodium sulfate and concentrated. LC (SiO2, 3:1 cyclohexane/methylene chloride) gives 0.98 g of product (28.6percent yield).1H NMR (CD2Cl2, 400 MHz): delta=8.75 (s, 1H), 8.24 (s, 1H), 8.1 (dd, 2H), 7.67 (d, 1H), 7.48-7.55 (m, 6H).

The synthetic route of 2,2-Diethoxy-N,N-dimethylethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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Reference of 101-84-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 101-84-8, name is Diphenyl oxide belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6; Preparation of Partially brominated DPO[0056] To the 500 mL flask (equipped as described in Example 4) containing 47.3 g of DPO was added over about 10 minutes, 28.0 g of bromine with stirring and cooling at room temperature. Catalyzed Bromination [0057] In a 1 -liter jacketed flask equipped with mechanical stirrer, Friedrich condenser(water cooled at about 250C), and with a 1/32-inch diptube but without a fractionation column were placed 3.8 g of AlCl3 and 885 g of bromine. After a feed time of about 7.25 hours, all of the partially brominated DPO had been fed from the flask. The reaction temperature was maintained at 56.30C to 57.20C throughout the addition. The reaction mixture was refluxed for 4 minutes as the temperature rose to 58.40C, then 450 mL of water was added and the reactor was set for distillation. The product was distilled to 1700F (about 770C) and 312 g of bromine was collected. The water layer was decanted from the reactor, 400 mL of water was added, stirred, and discarded. Then 400 mL of water and 10 g of NaOH were added, the mixture was stirred well and product was collected and water washed on a filter. GC analysis showed the product was composed of 99.71% of decabromodiphenyl oxide, and 0.034 and0.259% of the first and second nonabromodiphenyl oxide isomers, respectively. The product was placed in a 1250C oven and after drying overnight weighed 252.0 g. EXAMPLE 7Preparation of Partially brominated DPO [0058] To the 500 mL flask (equipped as described in Example 4) containing 49.1 g of DPO was added over aboutlO minutes, 29.7 g of bromine. This was purged with nitrogen to remove HBr. Catalyzed Bromination[0059] In a 1 -liter jacketed flask equipped as in Example 6 (no fractionation column) were placed 3.8 g of AlCl3 and 884 g of bromine. The mixture was heated to 59C and a feed of the partially brominated DPO formed above was initiated. The feed through the 1/32-inch diptube was set at a rate of about 0.21 mL per minute. All the partially brominated DPO was added over 3 hours and 23 minutes, The reaction mixture had been maintained at a temperature of 56.10C to 57.10C throughout the addition time reflux was continued for about 10 more minutes as the temperature rose to 59.60C. Then 450 mL of water was added to the reaction mixture and the reactor was set for distillation. The mixture was distilled to 770C and 294.5 g of bromine was collected. The mixture was worked up as in Example 6. GC analysis of the product showed 99.59% of decabromodiphenyl oxide and 0.11% and 0.296% of first and second nonabromodiphenyl oxide peaks, respectively. Present in the product were a few “lumps”. One was removed and a GC showed it contained 99.61% of decabromodiphenyl oxide and 0.100 and 0.291% of the first and second nonabromodiphenyl oxide isomers, respectively. The product was oven dried. EXAMPLE 8Preparation of Partially brominated DPO [0060] To the 500 mL flask (equipped as in Example 4) containing 49.00 g of DPO was added 31.4 g of bromine over about 10 minutes. Then the mixture was purged with nitrogen. Catalyzed Bromination[0061] In a 1 -liter jacketed flask, equipped as in Example 6, were placed 3.82 g OfAlCl3 and 988 g of bromine The mixture was heated to 56.O0C and addition of the partially brominated DPO begun at a feed rate of about 0.18 mL per minute. This feed was maintained for a period of about 4 hours with the temperature fluctuating between 53.O0C and 54.O0C. The mixture was allowed to reflux for about another 7 minutes with the temperature reaching about 600C. Then, 450 mL of water was added to the reaction mixture and the reaction vessel was set for distilling bromine. The distillation was conducted to 770C whereby an amount of 400.2 g of bromine was recovered. Product was isolated as in Example 5 and oven dried. GC analysis showed 0.093% and 0.471% of the first and second nonabromodiphenyl oxide peaks, respectively, and 99.436% of decabromodiphenyl oxide. After drying over the weekend the product weighed 260.1 g.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diphenyl oxide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALBEMARLE CORPORATION; WO2008/27776; (2008); A2;,
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