Tag: M.W=100-200

Synthetic Route of 2741-16-4, 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. 2741-16-4, name is Isopropoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To 3-chloroperbenzoic acid dried in vacuo for 1 h prior to use (504mumol) in dry dichloromethane (5mL), was added 3-iododobenzoate succinimidyl ester (458mumol) and the solution was stirred at room temperature for 15min. Anisole (504mumol) was then added, the reaction cooled to -20C and triflic acid (916mumol) added. The solution turned dark. It was stirred for 15min at -20C and the volatiles were removed by rotary evaporation. To the dark residue was added Et2O. The thick oily suspension was stirred for about 45min upon which a deep blue precipitate formed. It was then purified by flash chromatography using aCH2Cl2/ tBuOH gradient from 95:5 to 60:40. The solid obtained was then recrystallized from CH3CN/Et2O to afford white crystals; 4.1.3 3-(Succinimidyloxycarbonyl)phenyl(4-isopropoxyphenyl)iodonium triflate (4b) The procedure was identical to the preparation of 4a, with anisole replaced by isopropoxybenzene and afforded 4b as colorless needles in 8% yield. 1H NMR (CD3CN, 400 MHz, ppm): delta 1.31 (d, 6H), 2.86 (s, 4H), 4.64-4.72 (m, 1H), 7.03 (d, 2H, J = 8.0 Hz), 7.72 (t, 1H, J = 8.0 Hz), 8.03 (d, 2H, J = 8.0 Hz), 8.35 (m, 2H), 8.74 (m, 1H). 13C NMR (CD3CN, 100 MHz, ppm): delta 21.9, 26.5, 72.0, 101.7, 115.1, 120.5, 123.6, 129.4, 134.0, 134.9, 137.0, 139.2, 141.7, 161.2, 163.1, 170.8. 19F NMR (CD3CN, 400 MHz, ppm): delta -79.70. HRMS: C20H19INO5+[M-OTf]+ calc: 480.0308, found: 480.0315

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, Isopropoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guerard; Navarro; Lee; Roumesy; Alliot; Cherel; Brechbiel; Gestin; Bioorganic and Medicinal Chemistry; vol. 25; 21; (2017); p. 5975 – 5980;,
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Synthetic Route of 2944-49-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2944-49-2 name is 1-Methoxy-2,3-dimethylbenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of the above crude product (2) (3.5g) in tetrachloromethane (C4Cl4) (100mL) at room temperature were added N-bromosuccinimide (NBS) (34.0g, 190.4mmol) and 2,2′-azobis(2-methylpropionitrile) (AIBN) (0.3g). The resulting reaction mixture was allowed to stir under reflux for 24h. After reaction completion, the reaction mixture was filtered and washed using the saturated NaHSO4 solution to remove the residual bromine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography to give a white solid (7.70 g, 72.4% in the two-step yield).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Methoxy-2,3-dimethylbenzene, and friends who are interested can also refer to it.

Reference:
Article; Jin, Chaobin; Alenazy, Rawaf; Wang, Yinhu; Mowla, Rumana; Qin, Yinhui; Tan, Jin Quan Eugene; Modi, Natansh Deepak; Gu, Xinjie; Polyak, Steven W.; Venter, Henrietta; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 29; 7; (2019); p. 882 – 889;,
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Application of 41365-75-7, 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 41365-75-7 as follows.

General procedure: A mixture of 0.6 mmol of quinomethane 1a-1c and 0.6 mmol of 3,3-diethoxypropan-1-amine (2) or 4,4-diethoxybutan-1-amine (3) in 1 mL of 1,4-dioxane was stirred for 2-3 h at room temperature under argon. When the reaction was complete, the solvent was removed under reduced pressure (water-jet pump), and the residue was washed with hexane and dried in a vacuum (oil pump) until constant weight.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Vagapova; Amirova; Burilov; Pudovik; Sinyashin; Russian Journal of Organic Chemistry; vol. 51; 9; (2015); p. 1268 – 1271; Zh. Org. Khim.; vol. 51; 9; (2015); p. 1294 – 1297,4;,
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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. 41365-75-7, name is 1-Amino-3,3-diethoxypropane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 41365-75-7

Intermediate 210: 6-Benzyl-/yt-(3,3-diethoxypropyn-/^-methylpyridine-2,4- dicarboxamide (1150) To a mixture of 2-benzyl-6-(methylcarbamoyl)isonicotinic acid (77.8 mg, 0.29 mmol) and HATU (142.9 mg, 0.38 mmol) in DMF (1.5 mL) was added 3,3-diethoxypropan-l-amine (0.061 mL, 0.37 mmol) and DIPEA (0.151 mL, 0.86 mmol). The mixture was stirred at rt for 4.5 h, after which the volatiles were evaporated under a stream of nitrogen. This was redissolved in DMSO (3 mL) and directly purified by MDAP (high pH). The required fractions were combined and evaporated in vacuo to give 6-benzyl-/V,-(3,3-diethoxypropyl)-Ae-methylpyridine-2,4-dicarboxamide (91.3 mg, 0.23 mmol, 79 % yield) a light brown gum. (1151) LCMS (2 min High pH): Rt = 1.08 min, [MH]+ = 400.4.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
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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. 366-99-4, name is 3-Fluoro-4-methoxyaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Fluoro-4-methoxyaniline

Acetone (11.6 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydride (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stirred at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 3-Fluoro-N-isopropyl-4-methoxyaniline (2.90 g, 79percent yield). 1H NMR (400 MHz, CDC13) delta ppm 6.84 (dd, J= 9.5, 8.7 Hz, 1H), 6.41 (dd, J= 13.5, 2.7 Hz, 1H), 6.33- 6.27(m, 1H), 3.83 (s, 3H), 3.54-3.52(m, 1H), 3.28 (s, 1H), 1.21 (d, J= 6.3 Hz, 6H).

The synthetic route of 366-99-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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Related Products of 148583-65-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 148583-65-7, name is 4-Fluoro-2-isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

(3) Synthesis of 1-(4-Fluoro-2-isopropoxyphenyl)piperazine Dihydrochloride By similar reaction and treatment to that in Example 40(3) using 4-fluoro-2-isopropoxyaniline instead of 4-fluoro-2-methoxyaniline, the title compound was obtained as purple crystals. 1H-NMR(DMSO-d6)delta: 1.31(6H, d, J=5.9 Hz), 3.25(8H, br.s), 4.67(1H, septet, J=5.9 Hz), 6.71(1H, dt, J=8.6, 2.6 Hz), 7.93(1H, dd, J=11, 2.6 Hz), 7.08(1H, dd, J=5.9, 2.6 Hz), 9.61(2H, br.s). IR(KBr): 3442, 2983, 2925, 1626, 1522 cm-1; MS(EI): 238(M+).

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-2-isopropoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Pharma Corporation; US6455528; (2002); B1;,
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Synthetic Route of 171290-52-1, The chemical industry reduces the impact on the environment during synthesis 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, I believe this compound will play a more active role in future production and life.

The mixture 1-ethynyl-3,5-dimethoxybenzene 1e (2 g, 12.3 mmol) was dissolved in acetonitrile (15 mL), and cooled down to 0 C., then a salt of 1-chloromethyl-4-fluoro-1,4-diazonium dicyclo 2.2.2 octane bis(tetrafluoroborate) (6.6 g, 18.5 mmol) was added in portions, then stirred at room temperature overnight, the reaction solution was poured into water (50 mL), and extracted with dichloromethane (30 mL*3), and the organic phases were combined and dried over anhydrous sodium sulfate, the desiccant was removed by filtering, next the system was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=30/1), so as to obtain the title product 1-ethynyl-2-fluoro-3,5-dimethoxybenzene 17a (800 mg, yellow solid), and the yield was 36%. 1H NMR (400 MHz, CDCl3) delta 6.46 (dd, J=6.9, 2.9 Hz, 1H), 6.41 (dd, J=4.5, 3.0 Hz, 1H), 3.78 (s, 3H), 3.69 (s, 3H), 3.22 (s, 1H).

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, 3,5-Dimethoxyphenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING INNOCARE PHARMA TECH CO., LTD.; Chen, Xiangyang; Gao, Yingxiang; Kong, Norman Xianglong; (59 pag.)US2019/210997; (2019); A1;,
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Related Products of 93-04-9, 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. 93-04-9, name is 2-Methoxynaphthalene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of bromine (first raw material storage tank 1) and 2-methoxynaphthalene in acetic acid (2-methoxynaphthalene in acetic acid solution(Second raw material storage tank 2) was successively passed through a microstructured mixer according to a molar ratio of 2-methoxynaphthalene and bromine of 1: 33,A heat exchanger 4,A tubular temperature control module 5 and a first microstructure reactor 6,In the first microstructure reactor 6Pressure and 55 C to stay 8. 5min reaction.at the same time,The first microstructure reactor 6 discharges the second microstructure reactor 7,In a second microstructure reactor 7 at atmospheric pressure and 85 C for 8 min,The second microstructure reactor 7 is discharged through a length of polytetrafluoroethylene capillary into the product collecting bottle 8,The polytetrafluoroethylene capillary was immersed in an ice-water bath to terminate the reaction.The second microstructure reactor is introduced into the ice water,A large number of solid precipitation,Filtration,Washed,The filter cake was dissolved in chloroform, washed with 10wt% Na0H aqueous solution, washed with water, dried over anhydrous sodium sulfate and evaporated to chloroform. The residue was recrystallized from anhydrous ethanol to give white needle crystals in a yield of 90.2% .

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

Reference:
Patent; Nanjing University of Technology; GUO, KAI; FANG, ZHENG; HE, WEI; OUYANG, PINGKAI; (7 pag.)CN103664542; (2016); B;,
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Reference of 2944-49-2,Some common heterocyclic compound, 2944-49-2, name is 1-Methoxy-2,3-dimethylbenzene, molecular formula is C9H12O, 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 solution of 2,3-dimethylanisole (10.00 g, 73.4 mmol) in acetonitrile (500 ml) was added to a mixture of copper(II) sulphate pentahydrate (18.14 g, 72.7 mmol) and potassium peroxodisulphate (59.81 g, 0.22 mol) in water (700 ml) and heated for 30 min at reflux. After cooling, water (100 ml) and dichloromethane (150 ml) were added and the phases were separated. The aqueous phase was extracted with dichloromethane (2×200 ml). The combined organic phases were dried over anhydrous sodium sulphate, filtered and concentrated on a rotary evaporator. 4:1 n-heptane/ ethyl acetate (200 ml) was added to the brown oil and this was filtered over silica gel. The filtrate was concentrated on a rotary evaporator. 4.63 g (30.8 mmol; 42%) of a gradually crystallizing yellowish oil was obtained.1H-NMR (CDCl3, 400 MHz): delta=10.63 (s, 1H; HC?O), 7.37 (t, 1H; J=8.0 Hz; Ar-H), 6.80 (m, 2H; Ar-H), 3.88 (s, 3H; O-CH3), 2.56 (s, 3H; Ar-CH3).13C-NMR (CDCl3, 100.6 MHz): delta=192.2 (C?O), 163.0 (Ar-C), 141.9 (Ar-C), 134.4 (Ar-CH), 123.9 (Ar-CH), 123.1 (Ar-C), 108.9 (Ar-CH), 55.6 (O-CH3), 21.4 (CH3).

The synthetic route of 2944-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ivoclar Vivadent AG; Moszner, Norbert; Hendrik, John; Lamparth, Iris; Barner-Kowollik, Christopher; Krappitz, Tim; Feist, Fiorian; (14 pag.)US2020/79888; (2020); A1;,
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Reference of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: Catalytic acetic acid was added to a stirred solution of the appropriate formyl pyrimidine (1 eq) (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-formylpyrimidin-2-yl)carbamate) and the appropriate benzyl amine (1.5 eq) (ex: l-(3-methoxyphenyl)-N-methylmethanamine) in 1 ,2-dichloroethane at 0C then followed by sodium cyanoborohydride (2 eq) was added then the reaction mixture was stirred at room temperature for 16h. After completion of the reaction, the reaction mixture was quenched with minimum amount of saturated sodium bicarbonate solution, the organic product was extracted with dichloromethane (3x). The combined organic extracts were dried over anhydrous sodium sulfate. Solvent was distilled under reduced pressure to give the crude compound. The crude was purified by flash column chromatography (10-20% ethyl acetate/petroleum ether or 2-5% methanol/dichloromethane) to get the desired BOC protected product (ex: tert-butyl (tert-butoxycarbonyl)(4-((tert-butoxycarbonyl)(p- tolyl)amino)-6-(((3-methoxybenzyl)(methyl)amino)methyl)pyrimidin-2-yl)carbamate). (0942) In some examples, the reaction was carried out with trimethyl orthoformate (10 eq) and sodium triacetoxyborohydride (2.5 eq).

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MINORYX THERAPEUTICS S.L.; GARCIA COLLAZO, Ana Maria; BARRIL ALONSO, Xavier; CUBERO JORDA, Elena; REVES VILAPLANA, Marc; ROBERTS, Richard Spurring; (213 pag.)WO2018/122775; (2018); A1;,
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