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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H5F3N2

Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (4) (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H2O, extracted with EtOAc (2 × 400 mL). The combined organic extracts were washed with saturated NaHCO3solution (2 × 300 mL) and brine (300 mL). The organic layer was dried over MgSO4and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from to give 55.8 g (73.9%) of (2R)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]- 2-hydroxy-2-methylpropanamide (8) as a light-yellow solid. M.p. 134.0-136.5C;1H NMR (CDCl3/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J = 10.8 Hz, 1H, CH2), 4.05 (d, J = 10.8 Hz, 1H, CH2), 7.85 (d, J = 8.4 Hz, 1H, ArH), 7.99 (dd, J = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). Calculated Mass: 349.99, [M – H] – 349.0.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; PAGADALA, Jayaprakash; DUKE, Charles B.; COSS, Christopher C.; DALTON, James T.; (296 pag.)WO2016/172358; (2016); A1;,
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Synthetic Route of 21883-13-6, A common heterocyclic compound, 21883-13-6, name is 4-Methoxy-2-methylbenzonitrile, molecular formula is C9H9NO, 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.

Description for D33 4-Hydroxy-2-methylbenzonitrile (D33)To a solution of 2-methyl-4-(methyloxy)benzo?iotat?le (7 g) in anhydrous DCM (100 mL) was added drapwise BBr3 (51 5 g) at -78 C The resulting mixture was allowed to warm to RT and stirred for 24 hours LCMS indicated the reaction was completed Water was added dropwise slowly to quech the reaction. The mixture was extracted with EA (3×100 mL) and the combined organic layer was washed with brine dried over sodium sulfate, and concentrated to give 5 4 g of 4-hydroxy-2-methylbenzo nitrile (D33) as a white solid. deltaH (DMSO-Cf6, 400MHz). 2.45(3H, s), 6.67(1H1 d), 6 69(1H1 d), 7 51(1H, d), 1043(1H1 s). MS (ES) C8H7NO requires 133, found 134 1 (M+ H+)

The synthetic route of 21883-13-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; XIANG, Jianing; LIN, Xichen; REN, Feng; DENG, Guanghui; WO2010/148650; (2010); A1;,
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Related Products of 22364-68-7, 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. 22364-68-7 name is 2-(o-Tolyl)acetonitrile, 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.

Example 6: (E/Z)-2-(2-methylcvclohexylidene)-2-o-tolylacetonitrile To the stirred mixture of 2-methylcyclohexanone (12.3 g, 0.11 mol) and o-methyl benzyl cyanide (13.1 g, 0.10 mol) is added sodium methoxide (30% in MeOH, 18.5 ml, 0.10 mol) during 15 min and the resulting brown mixture is heated under stirring to 600C (oilbath) for 3 h and 8O0C for further 10 h. The mixture is diluted with toluene, the organic layer washed with brine/H2O 1 :1 and dried over MgSO4. The solvent is removed under reduced pressure and the residue distilled over a short-path apparatus at 0.05 mbar. The fraction distilling at 96-1240C is collected (5.4 g) and further purified by EPO flash chromatography on SiO2, eluting with cyclohexane/methyl-t-butyl ether 9:1. After removal of the solvent, the residue is bulb-to-bulb distilled at 175C (0.05 mbar) to yield 2.19 g (9%) of colourless oil, which consists of E/Z-isomers (not attributed) in a 54:46 ratio (GC). The NMR-spectra indicates also the presence of distinguishable rotamers (atropisomers) at room temperature.Odour description: balsamic, sweet, cinnamic, plum.13C-NMR (100 MHz, CDCI3) (E/Z-mixture and atropisomers at room temperature): 166.6, 166.4, 166.3 (s), 136.7, 136.6 (s), 133.1 , 133.0 (s), 130.4, 130.3, 130.3 (d), 130.0, 129.8, 129.6, 129.3 (d), 128.6, 128.5 (d), 126.1 , 126.0 (d), 117.7, 117.7, 117.6, 117.5 (s), 106.2, 106.1 , 105.9 (s), 36.2, 36.1 (d), 33.2, 33.1 (t), 32.7, 32.3 (d), 29.8, 29.8 (t), 28.3, 28.2 (t), 27.4 (t), 26.8, 26.2 (t), 20.0, 20.0, 19.9, 19.9 (t), 19.5, 19.5 (q), 19.2 (q), 18.6, 18.5 (q), 18.1, 17.4 (q).MS (main isomer): 25 (100, [M+]), 210 (86), 196 (26), 182 (40), 168 (57), 154 (70).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(o-Tolyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GIVAUDAN SA; WO2006/133592; (2006); A1;,
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Application of 50846-36-1, 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 50846-36-1 as follows.

200 g of 2-amino-2-methylpropionitrile hydrochloride was added to a 3. 0 L round bottom flask and 1.5 g of methanol and 167 g of triethylamine were added to the reaction flask again, and the reaction solution was cooled to 10 And then 325 g of di-tert-butyl dicarbonate was added dropwise to the reaction solution at room temperature for 2. 0 h, and the temperature was raised to reflux 3. Oh; TLC detection, the reaction was complete and concentrated under reduced pressure. The remaining solid was dissolved with ethyl acetate, The aqueous layer was washed twice with ethyl acetate and the combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 190 g.

According to the analysis of related databases, 50846-36-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing wedo Pharmaceutical Co. Ltd.; Bao, jin yuan; song, zhi chun; Jiang, yuwei; Zhang, xiaoqing; (5 pag.)CN104016885; (2016); B;,
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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. 58949-75-0, name is 4-(2-Oxopropyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 58949-75-0

(a) 4-(1-Bromo-2-oxopropyl)benzonitrile Bromine (5.28 g) in dichloromethane (80 ml) was, added dropwise at 25 C. over 1 hour to 4-(2-oxopropyl) benzonitrile in dichloromethane (85 ml). The reaction mixture was stirred for 1/2 hour after the addition was complete. The mixture was washed with brine (50 ml), dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound as a pale red oil (7.55 g, 96%). 1 H-NMR (CDCl3): 2.41 (s, 3H); 5.24 (s, 1H); 7.61 (d, J=4 Hz), 2H); 7.73 (d, J=4 Hz, 2H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 58949-75-0.

Reference:
Patent; Pfizer Inc.; US4935430; (1990); A;,
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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. 29509-06-6, name is 4-Methyl-3-oxopentanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Methyl-3-oxopentanenitrile

Under nitrogen atmosphere, the compound of Example 2A (8.03g, 72mmol) was dissolved in alcohol (50 mL). Methylhydrazine (3.32g, 72mmol) was added. The resultant mixture was slowly warmed and refluxed with stirring. The reaction was kept for 3 hr. The reaction was stopped and cooled to room temperature. Alcohol was rotary-evaporated to obtain a crude product as oil. The crude product was purified with column chromatography (eluant: petroleum ether/ethyl acetate = 1: 1) to give 5.2 g of the title compound. MS (ESI): m/z 140 (M+H)+

The synthetic route of 29509-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hande Starlake Bioscience Co., Ltd.; Hande Pharma Limited; LI, Chenxi; SHEN, Weisheng; FANG, Yang; LE, Xiaoyong; EP2578587; (2013); A1;,
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Synthetic Route of 85363-04-8,Some common heterocyclic compound, 85363-04-8, name is N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, molecular formula is C7H12N2O2, 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.

N-BOC-Glycinonitrile [sic] (12.0 g, 76.8 mmol) and diethylamine (0.16 ml, 2.1 mmol) were dissolved in toluene (100 ml). The solution was cooled to -10 C., saturated with hydrogen sulfide and subsequently stirred overnight at room temperature. The precipitate formed was filtered off with suction and washed with toluene. The product was dried in vacuo at 45 C. Yield: 13.2 g (69.4 mmol, 90.3%, yellowish solid)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(tert-Butoxycarbonyl)-2-aminoacetonitrile, its application will become more common.

Reference:
Patent; Abbott GmbH & Co., KG; US6740647; (2004); B1;,
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Some common heterocyclic compound, 1735-88-2, name is 2-Cyano-N-(4-fluorophenyl)acetamide, molecular formula is C9H7FN2O, 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. COA of Formula: C9H7FN2O

A mixture of N-(4-fluorophenyl)cyanoacctamide (1 equiv.), hydroxylamine hydrochloride (2 equiv.) and tricthylamine (2 equiv.) in DMF was heated to 50-60nC for 4 h th«n diluted with water and the product filtered off and dried.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1735-88-2, its application will become more common.

Reference:
Patent; COMMONWEALTH SCIENTIFIC AND INDUSTRIAL RESEARCH ORGANISATION; WO2008/70891; (2008); A1;,
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Application of 2941-29-9,Some common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, 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.

[00482] Step B: Preparation of 2-(l -methyl- lH-pyrazol-4-ylV2.4.5.6- tetrahydrocyclopenta- [c]pyrazol-3-amine : To a solution of di-tert-butyl 1 -(1 -methyl- 1H- pyrazol-4-yl)hydrazine-l,2-dicarboxylate (103 mg, 0.330 mmol) in EtOH (1.65 mL, 0.330 mmol) was added concentrated HCl (137 mu, 1.65 mmol). The mixture was stirred at ambient temperature for 5 minutes, then cooled in an ice bath followed by addition of 2- oxocyclopentanecarbonitnle (36.0 mg, 0.330 mmol). After stirring for 5 minutes, the reaction mixture was warmed to ambient temperature overnight. The reaction mixture was concentrated and partitioned in water and DCM. After phase-separation, the aqueous layer was basified (pH 10) and then extracted with DCM (3 x 10 mL). The combined organic extracts were dried with MgS04, filtered and concentrated in vacuo. The crude material was purified by reverse-phase column chromatography, eluting with 0-100percent acetonitrile/water to afford the product as a yellow solid (4.5 mg, 6.7percent yield). MS (apci) m/z = 204.1 (M+H).

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

Reference:
Patent; ARRAY BIOPHARMA INC.; ALLEN, Shelley; BRANDHUBER, Barbara J.; CONDROSKI, Kevin Ronald; HUANG, Lily; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78408; (2014); A1;,
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Related Products of 41963-20-6,Some common heterocyclic compound, 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, molecular formula is C8H6BrN, 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 4-bromo-3-methyl-benzonitrile (commercially available) (500 mg) in dichloromethane (7.5 ml) was added at 00C to a solution of diisobutylaluminium hydride (“DIBAL-H”) (2.6. ml) in hexanes (IM). The reaction mixture was stirred at 00C for 2 hours. The reaction mixture was poured on a mixture of ice (10 g) and aqueous hydrobromic acid (6M) (10 ml). The mixture was allowed to warm to ambient temperature and then extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate, and concentrated to give 4-bromo-3-methyl-benzaldehyde (0.419 g) as a colorless oil. 1H-NMR (400 MHz, CDCl3): 9.95 (s, IH), 7.72 (m, 2H), 7.55 (d, IH), 2.50 (s, 3H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3-methylbenzonitrile, its application will become more common.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; EL QACEMI, Myriem; BOBOSIK, Vladimir; RENOLD, Peter; CASSAYRE, Jerome, Yves; JUNG, Pierre, Joseph; WO2010/20521; (2010); A1;,
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