Tag: M.W=100-200

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1515-95-3 as follows. name: 1-Ethyl-4-methoxybenzene

General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 muL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 % aq tert-butyl hydroperoxide (200 muL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4).

According to the analysis of related databases, 1515-95-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hossain, Md. Munkir; Shyu, Shin-Guang; Tetrahedron; vol. 72; 29; (2016); p. 4252 – 4257;,
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767-91-9, name is 2′-Methoxyphenyl acetylene, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C9H8O

General procedure: Ferric sulfate hydrate (I, 8 mol%), glacial acetic acid (5 mL) and the alkyne (1 – 2 mmol) were introducedinto a 50 mL Schlenk tube, equipped with an air condenser, and the mixture kept under stirring at 95 C or120 C, until consumption of the substrate or no further conversion, as evidenced by TLC or GC. Uponcooling, the supernatant solution was poored into water and the residue washed twice with diethyl ether.After extraction with diethyl ether ( 2), the combined organic layers were washed with a saturated aqueoussolution of sodium bicarbonate and then water until neutrality. Alternatively, the crude from the reactions ofsubstrates featuring hydroxyl or carbonyl groups, as for 12, 15, 20 and 22, was obtained by removing aceticacid under vacuum, in order to reduce loss of material during biphasic extraction. The products were purified

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bassetti, Mauro; Ciceri, Samuele; Lancia, Federico; Pasquini, Chiara; Tetrahedron Letters; vol. 55; 9; (2014); p. 1608 – 1612;,
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Application of 7664-66-6, 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. 7664-66-6, name is 4-Isopropoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 54: Preparation of 2-[l-(4-fluorophenyl)-3-[2-(4-methoxyphenyl)ethyl]-5- oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(propan-2-yloxy)phenyl]acetamide. – EDCI (143 mg; 0.74 mmol; 1.5 eq), followed by HOBt (113 mg; 0.74 mmol; 1.5 eq), DIPEA (256 muU 1-49 mmol; 3 eq) and 4-(propan-2-yloxy)aniline (150 mg; 0.99 mmol; 2 eq) were added to a solution of 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl] -5-oxo-2-sulfanylideneimidazolidin-4-yl] acetic acid (1-21 ) (200 mg; 0.50 mmol; 1 eq) in anhydrous dioxane (8 mL). The reaction mixture was stirred at room temperature for 18 hours. Saturated ammonium chloride (20 mL) was added and the aqueous layer was extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with saturated sodium chloride (3 x 20 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was purified on silica gel using dichloromethane/ethyl acetate (95/5) as an eluent. After trituration in diethyl ether/ethanol, the title compound 2-[l-(4-fluorophenyl)-3-[2-(4- methoxyphenyl)ethyl]-5-oxo-2-sulfanylideneimidazolidin-4-yl]-N-[4-(propan-2- yloxy)phenyl]acetamide was obtained with 43% yield (114 mg) as a white solid. 1H- NMR (Acetone-d6): delta (ppm), 1.26 (d, 6H), 2.94 (m, 1H), 3.15 (m, 2H), 3.36 (m, 1H), 3.74 (s, 3H), 3.78 (m, 1H), 4.31 (m, 1H), 4.59 (m, 2H), 6.86 (d, 4H) , 7.25 (m, 4H), 7.48 (m, 4H), 9.32 (s, 1H); MS (ESI+): m/z = 535.9 [M+H]+ .

The synthetic route of 4-Isopropoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VIVALIS; GUEDAT, Philippe; BERECIBAR, Amaya; CIAPETTI, Paola; VENKATA PITHANI, Subhash; TROUCHE, Nathalie; WO2013/171281; (2013); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 6298-96-0 as follows. Computed Properties of C9H13NO

(a). ( 1 S)-JV- r 1 -(4-Methoxy-phenyl>ethyll -3 -oxo-butyramide; To a solution of (S)-l-(4-methoxy-phenyl)-ethylamine (25 g) in dichloromethane (60 mL) was added TEA (20 g) and DMPA (200 mg). Then a solution of 4-methylene- oxetan-2-one (16.7 g) in dichloromethane (60 ml) was added over a period of 30 minutes and then stirred at 20 0C for 18 h. The mixture was washed with IM HCl, aq. NaHCO3 and aq. NaCl. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. EPO Yield: 39.8 g. MS-ESI: [M+H]+ = 236

According to the analysis of related databases, 6298-96-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N.V. ORGANON; WO2006/117368; (2006); A1;,
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Synthetic Route of 22483-09-6, The chemical industry reduces the impact on the environment during synthesis 22483-09-6, name is 2,2-Dimethoxyethanamine, I believe this compound will play a more active role in future production and life.

(3,4-Methylenedioxybenzylidene)-(2,2-dimethoxyethyl)amine (11b). Aminoacetaldehyde dimethylacetal (7.10 g, 0.0666 mol) was dissolved in chloroform (50 mL) and MgSO4 (12 g) was added. Then piperonal (10b, 10.10 g, 0.0666 mol) was added and the mixture was stirred at room temperature. After 24 h there still was unreacted piperonal in the reaction mixture and more amine (6.00 g) was added. The reaction mixture was stirred again at room temperature for 24 h and since there still was some piperonal present more amine (6.00 g) was added again. After stirring the reaction mixture for another 24 h at room temperature the imine was isolated. The reaction mixture was diluted with water (300 mL) and the organic layer was washed with water 200 mL*2, brine (200 mL) dried Na2SO4 and concentrated to provide the pure imine as a yellow oil (15.80 g, 100%). 1H NMR (300 MHz, CDCl3) delta 8.13 (s, 1H), 7.33 (s, 1H), 7.07 (d, J=8.10 Hz, 1H), 6.78 (d, J=8.10 Hz, 1H), 5.96 (s, 2H), 4.62 (t, J=5.4 Hz, 1H), 3.70 (d, J=4.2, 2H), 3.83 (s, 6H).

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, 2,2-Dimethoxyethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cushman, Mark S.; Ioanoviciu, Alexandra S.; Pommier, Yves G.; US2008/242692; (2008); A1;,
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Related Products of 37466-89-0,Some common heterocyclic compound, 37466-89-0, name is 3-Methoxybenzene-1,2-diamine, molecular formula is C7H10N2O, 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.

A mixture of 2-methoxy-6-nitroaniline (1 g, 5.95 mmol), 10% palladium carbon (300 mg) and methanol (25 ml) was stirred in a hydrogen atmosphere for 4 hours. The reaction vessel was purged with nitrogen and a catalyst was removed by filtration. To the reaction mixture, carbon disulfide (15 ml) was added and the mixture was stirred at room temperature overnight. Triethylamine (1 ml) was added to the reaction mixture, which was stirred at 50 C. for 3 hours. After the reaction mixture was concentrated, methanol (2 ml) and diethyl ether (20 ml) were added to the residue. The generated solid was collected by filtration to obtain the title compound (950 mg, yield: 88.6%) as a light orange solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxybenzene-1,2-diamine, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; US2007/10542; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 22236-10-8, name is 4-(Difluoromethoxy)aniline, 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 22236-10-8, Safety of 4-(Difluoromethoxy)aniline

To a mixture of 9 (190 mg, 0.74 mmol), 4-(difluoromethoxy)aniline (5a, 130.5 mg, 0.82 mmol) and 4-(dimethylamino)pyridine (DMAP) (99.4 mg, 0.81 mmol) in dimethylformamide (DMF) (3 mL) was added N’-ethylcarbodiimide hydrochloride (EDO HC1 (156 mg, 0.81 mmol), the mixture was stirred at room temperature for 1 h. Then, 100 mL water was added to the reaction mixture to form off-white precipitate, which was collected on a filter to give an off- white solid. The solid was dissolved in ethyl acetate and dried over MgS04, filtered, and the solvent was removed by rotary evaporator. The crude product was purified by recrystallization from ethyl acetate/hexane to afford 2a as white solid (120.4 mg, 41% yield): mp. 174- 177 C; 1H NMR (500 MHz, CDC13) delta 0.92 (t, J = 7.5 Hz, 3H), 1.64 (m, 2H), 2.06 – 2.22 (m, 2H), 2.42 (t, = 7.5 Hz, 2H), 2.49 (t, = 6.9 Hz, 2H), 3.31 (t, = 5.7 Hz, 2H), 6.01 (s, 1H), 6.45 (t, = 74.0 Hz, 1H), 7.07 (d, J = 8.6 Hz, 2H), 7.55 (d, J = 8.6 Hz, 2H), 7.92 (s, 1H), 12.69 (s, 1H). 13C NMR (125 MHz, CDCI3) delta 13.8, 21.1, 24.8, 30.2, 35.5, 39.7, 107.8, 116.1(t, = 259 Hz), 120.6, 121.3, 135.6, 147.3, 160.2, 165.5, 169.9, 170.5; 19F NMR (376 MHz, CDCI3) delta -80.7; HRMS (ESI+) calcd for C18H22F2N3O3S [M + H]+ 398.1344, found 398.1345 (Delta = -0.03 ppm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Difluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; THE RESEARCH FOUNDATION FOR THE STATE UNIVERSITY OF NEW YORK; OJIMA, Iwao; ALFORD, Vincent; KAMATH, Anushree; CAO, Jian; REN, Xiaodong; SAMPSON, Nicole; AWWA, Monaf; (63 pag.)WO2018/175670; (2018); A1;,
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Some common heterocyclic compound, 2734-70-5, name is 2,6-Dimethoxyaniline, molecular formula is C8H11NO2, 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. SDS of cas: 2734-70-5

Trimethylalurninum (4.7 mL, 9.4 mmol) was added dropwise to a solution of 2,6-dimethoxyaniline (1.2 g, 7.8 mmol) and Compound lb (0.80 g, 9.4 mmol) in toluene (10mL) while cooling in an ice bath. After addition was complete, the reaction mixture was warmed to 110 °C and was stirred at this temperature for l4hrs. The cooled reaction mixture was partitioned between a saturated solution of Rochelle?s salt and EtOAc. The organic phase was separated, dried over MgSO4, filtered and concentrated under reducedpressure. The resulting residue was added to a silica gel (120 g) colunm and was eluted with 0-20percent of 20percent MeOH/DCM in 0.5percent TEA/DCM to give Compound lc (1.1 g, 4.5 mmol, 57 percent) as a brown liquid. MS ,n/z 239.0 (M+H). 1H NMR (500M1-lz, CDC13) 67.01(t, J 8.3 Hz, 1H), 6,62 (d, J= 7.7 Hz, 2H), 5.32 (s, 2H), 4.88 (hr s, 2H), 4.31 (s,2H), 3.82 (s, 6H), 3.62-3.73 (m, 2H), 1.19-1.33 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2734-70-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MENG, Wei; CHAO, Hannguang J.; FINLAY, Heather; LAWRENCE, R., Michael; MYERS, Michael C.; (154 pag.)WO2017/96130; (2017); A1;,
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Related Products of 1484-26-0,Some common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

Specifically, a solution of 3-benzyloxyaniline 2e (0.84 g, 4.2 mmol) and diphenylcyanocarbonimidate 1 (1.0 g, 4.2 mmol) in 2-PrOH (15 ml_) was stirred at ambient temperature under N2. After 5 h, the solids were collected by filtration washing with cold 2-PrOH to afford 3e (1.25g, 86percent) as a white solid: 1H NMR (300 MHz, DMSO- d6) delta 7.47-7.26 (m, 12H), 7.17 (s, 1H), 7.05 (d, J = 7.9 Hz, 1H), 6.90 (d, J = 8.3 Hz, 1H), 5.10 (s, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Benzyloxyaniline, its application will become more common.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; WO2007/30680; (2007); A2;,
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Related Products of 402-52-8,Some common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, molecular formula is C8H7F3O, 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 12 Production of 2-Methoxy-5-(trifluoromethyl)acetophenone 97.0 g (0.65 moles) of trifluoromethanesulfonic acid were put into a 200 ml three-necked flask. The flask was equipped with a reflux condenser, a dropping funnel and a thermometer and was connected with a calcium chloride tube for shielding the flask against moisture of the outside. A mixture of 22.8 g (0.13 moles) of 4-(trifluoromethyl)anisole and 26.5 g (0.26 moles) of acetic anhydride was added in a dropwise manner at a temperature of not higher than 30 C. to the flask under stirring. After the adding, the reaction was conducted for 3 hrs at 20-25 C. The resulting reaction liquid was poured into 300 ml of iced water. Then, 200 ml of ether were added to extract the reaction product. Then, 100 ml of ether were added to the aqueous layer to extract the reaction product again. The resulting two ether layers were combined together, followed by washing with 10% sodium hydrogencarbonate aqueous solution until the ether layer is made basic.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methoxy-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Central Glass Company, Limited; US2003/109574; (2003); A1;,
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