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 19179-31-8 as follows. 19179-31-8

Step 2: 3,5-dihydroxybenzonitrile To a solution of 3,5-dimethoxybenzonitrile (2 g, 2.2 mmol) in dichloromethane (20 mL) was added slowly BBr3 (15 mL, 1 M, 15 mmol) at -50 C. under N2. After addition, the mixture was stirred at -50 C. for 2 h and stirred at r.t for 20 hr. The mixture was slowly poured into ice-water with stirring and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column (petroleum ether/ethyl acetate (2:1) as eluent) to afford 3,5-dihydroxybenzonitrile (1.43 g). 1H NMR (DMSO-d6, 400 MHz): delta 10.02 (s, 2H), 6.56 (d, J=2.0 Hz, 2H), 6.51 (t, J=2.0 Hz, 1H).

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arrington, Kenneth L.; Burgey, Christopher; Gilfillan, Robert; Han, Yongxin; Patel, Mehul; Li, Chun Sing; Li, Yaozong; Luo, Yunfu; Lei, Zhiyu; US2014/100231; (2014); 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 218632-01-0 as follows. 218632-01-0

Compound 161a: 3-Fluoro-4-nitro-benzamide: The urea/hydrogen peroxide complex (22.65 g, 240.8 mmol, 2.0 eq) was added to a solution of 3-fluoro-4-nitro-benzonitrile (20.0 g, 120.4 mmol, 1.0 eq) and potassium carbonate (33.28 g, 240.8 mmol, 2.0 eq) in 20% water/acetone (500 ml). The reaction was stirred at room temperature for 22 hours when urea/hydrogen peroxide complex (11.33 g, 120.4 mmol, 1.0 eq) and potassium carbonate (16.64 g, 120.4 mmol, 1.0 eq) were added. The reaction was stirred for a further 2 hours at room temperature then diluted with water (300 ml) and DCM (500 ml). The organic layer was removed and the aqueous extracted with DCM (2 x 500 ml). The organics were combined, washed with brine, dried over sodium sulphate, and the solvent removed in vacuo to give the title compound as an orange solid (14.065 g, 76.31 mmol, 63%). 1H NMR shows product in >95% purity.

According to the analysis of related databases, 218632-01-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DEVELOGEN AKTIENGESELLSCHAFT; WO2006/136402; (2006); A1;,
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A common compound: 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4640-67-9

In a 25 mL reaction tube with a Teflon magnetic stir bar,Add 0.5 mmol of 4-fluorobenzoylacetonitrile, 0.5 mmol of 3-bromo-1,1,1-trifluoroacetone, 0.5 mmol of sodium acetate,Finally, 58 mmol of 1,4-dioxane was added, and the reaction was stirred at room temperature for 8 hours.Add 15 mL of water, extract three times with 10 mL of ether, and combine the organic phases.Washing with saturated sodium chloride solution, drying over anhydrous magnesium sulfate, and then removing the organic solvent by rotary evaporation;The obtained crude product was eluted with n-pentane and ethyl acetate (10:1, v/v).2-(4-Fluorophenyl)-5-hydroxy-5-(trifluoromethyl)-4,5-dihydrofuran-3-carbonitrile was isolated by silica gel column chromatography (yield: 76%).

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, 4640-67-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Fuzhou University; Weng Zhiqiang; Wang Junwen; (29 pag.)CN110272400; (2019); A;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., 127946-77-4

b) (2S,4S)-4-Hydroxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2 [0151] [0152] To the (2S,4R)-4-methanesulfonyloxy-1-(1-trifluoromethyl-cyclopropanecarbonyl)-pyrrolidine-2-carboxylic acid methyl ester (71.9 g, 200 mmol) were added under stirring and ice-cooling 2.0 M NaOH (120.0 mL, 240.0 mmol) all at once. The ice bath was removed and the white suspension was stirred at room temperature for 1 h. After neutralization by the addition of 2.0 M HCl (20.0 mL, 40.0 mmol; pH 7), 1-aminocyclopropanecarbonitrile hydrochloride (23.7 g 200 mmol) and sodium 2-ethylhexanoate (37.7 g, 220 mmol) were added all at once and the biphasic reaction mixture was stirred at 70 C. for 22 h and then cooled to 35 C. Dichloromethane (100 mL) and NaCl (16 g) were added and stirring was continued until the NaCl was dissolved (15 min). After acidification with 25% HCl (12 mL, pH 1), the reaction mixture was extracted with dichloromethane (3¡Á200 mL) and all three organic layers were washed separately with 5% NaHCO3 (40 mL pH 8). The combined organic layers were dried (Na2SO4), filtered, and evaporated (35-50 C./?5 mbar), affording beige, crystalline residue (88.5 g) which was dissolved in isobutyl acetate (500 mL) at -110 C. Crystallization, which started after seeding and cooling, was completed by stirring at room temperature for 1 h and at -20 C. for 4 h. Filtration and washing with cold isobutyl acetate gave after drying (10 mbar/55 C./4 h) the title product (47.7 g, 72.0%) as an off white, crystalline powder, mp. 156-157 C. [alpha]D20=-68.9 (c 1.0; CHCl3). 1H NMR (CDCl3, 400 MHz) delta 1.15-1.45 (m, 6H), 1.50-1.60 (m, 2H), 2.17-2.29 (m, 2H), 3.72 (dd, J1=11.8 Hz, J2=4.0 Hz, 1H), 3.98 (d, J=11.8 Hz, 1H), 4.40-4.52 (m, 2H), 4.95 (d, J=9.7 Hz, 1H), 7.93 (s, 1H). ESI-MS (m/z) [M+H]+332 (56).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hoffmann-La Roche Inc.; Bartels, Bjoern; Bliss, Fritz; Cueni, Philipp; Pfleger, Christophe; Zutter, Ulrich; US2013/123512; (2013); A1;,
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96606-37-0, A common heterocyclic compound, 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, molecular formula is C7H2F3N, 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.

Example 3: Synthesis OF 3-AMINO-6- (4-AMINO-PIPERIDIN-1-YL)-4-FLUORO- BENZOLB] THIOPHENE-2-CARBOXYLIC acid amide H N i N O F NHZ NN O N i HN 0- HS-NH, N F N O F F THF, 50 C, 3h DMF, 15h F 0A0 F NH2 HCI NH2 na ff) / MeOH, 3 days 0 H2N~ 3 ‘3 To a solution of 1.0 g (6.4 mmol) of 2, 4,6-trifluorobenzonitrile in MEOH (25 mL) was added 1.3 g (6.5 mmol) OF 4-N-BOC-AMINO-PIPERIDINE along with 1.2 mL (6.7 mmol) of N, N-diisopropylethylamine. The mixture was stirred at room temperature for 3 days then concentrated under reduced pressure to provide a white, solid. The solid was washed with large amounts OF H20 and dried under vacuum. The solid was RECRYSTALLIZED from hexane /EtOAc to provide 1.23 g (56%) of [1- (4-CYANO-3, 5-difluoro-phenyl) -piperidin-4-yl]- carbamic acid tert-butyl ester as a white solid.

The synthetic route of 96606-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/12283; (2005); A1;,
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4435-14-7,Some common heterocyclic compound, 4435-14-7, name is 2-Cyclohexylacetonitrile, molecular formula is C8H13N, 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.

Cyclohexyl acetonitrile (a-1) 18g, 2- chloro-benzoyl cyanide (b-1) It was mixed 24g and dichloromethane 700 mL, and cooled to -10 C..Then, after added dropwise over 70 min titanium tetrachloride 82g at the same temperature, was added dropwise over 2 hours N- methylmorpholine88 g, was stirred at room temperature for 15 hours. The reaction mixture was poured into water, stirred and added with chloroform, and filtered theinsoluble matter. The resulting filtrate the aqueous solution of sodium bicarbonate, washed sequentially with water, and then concentrated. By theresulting concentrate is purified by column to give the trans-1- cyclohexyl-2- (2-chlorophenyl) -1,2-dicyano ethylene (c-1) 18.1g.

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

Reference:
Patent; YAMADA CHEMICAL COMPANY LIMITED; HASE, TOMOYUKI; (19 pag.)JP2016/11348; (2016); A;,
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67515-59-7,Some common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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.

Preparation of BB7: 4-Fluoro-N-hydroxy-3-trifluoromethyl-benzamidine:BB7; To a solution of the 4-fluoro-3-trifluoromethyl-benzonitrile (20.0 g, 105.8 mmol) in ethanol (400 mL) a solution of the NH2OH-HCl (8.0 g, 116.4 mmmol) which was adjusted to pH=7.0 by addition of NaOH in H20 (8 mL) was added. The mixture was stirred vigorously and heated to about 65 C for about 16 h. The analysis by TLC indicated the completion of the reaction; it was concentrated to remove the solvent. The residue was redissolved in DCM (200 mL) and washed with water, brine and dried over Na2S04, concentrated in vacuum to afford 4-Fluoro-N-hydroxy-3-trifluoromethyl-benzamidine (BB7) as pale-yellow solid. 1H NMR (400 MHz, DMSO) delta ppm 9.83 (1H, s), 8.00 – 7.98 (2H, m), 7.50 (1H, t) and 6.00 (2H, s).

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

Reference:
Patent; ABBOTT LABORATORIES; CUSACK, Kevin, P.; BREINLINGER, Eric, C.; FIX-STENZEL, Shannon, R.; STOFFEL, Robert, H.; WOLLER, Kevin, R.; WO2011/71570; (2011); A1;,
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16532-79-9, 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. 16532-79-9, name is 4-Bromophenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a suspension of NaH (2.55 g, 63.75 mmol, 60%) in dimethyl sulfoxide (50 mL) were added dropwise a mixture of 4-bromophenyl-acetonitrile (223) (5 g, 25.51 mmol) and 1,4-dibromobutane (3.04 mL, 25.51 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (50 mL) at 0 C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water (20 mL) and 10% HCl solution (50 mL) were added to the mixture and the mixture was extracted with ethyl acetate (2¡Á200 ml). The organic layer was dried over Na2SO4, concentrated and purified by 100-200 silica column chromatography using hexane as the eluent to give 1-(4-bromophenyl)-cyclopentanecarbonitrile (224) (5.7 g, 89%) as a white crystalline solid. [0870] GC-MS: 250 (M+)

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

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); 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 874-89-5 as follows. 874-89-5

Example 99 N-((4-(hydroxymethyl)phenyl)methyl)-N-(1-methylpiperidin-4-yl)-2-(4-methoxyphenyl)acetamide hydrochloride (57MBT72D) To a stirred suspension of LiAlH4 (285 mg, 7.52 mmol) in diethylether (10 mL) at 0 C. was added a solution of 4-cyanobenzyl alcohol (0.5 g, 3.76 mmol) in diethylether (5 mL) over 15 min. The grey reaction mixture was heated to reflux for 3 h. After cooling to r.t., the mixture was treated successively with water (1 mL), 2M NaOH (2 mL) and water (2 mL) under vigorous stirring. The resulting white slurry was filtered and washed with CH2Cl2 (20 mL). Extraction with additional CH2Cl2 (20 mL) and n-butanol (20 mL) and evaporation yielded an oil, which upon flash chromatography (0-15% MeOH in CH2Cl2) gave 152 mg (29%) of 4-(aminomethyl)benzylalcohol (57MBT52B) as a white solid. Rf=0.51 (30% MeOH in CH2Cl2+3.5% NH4OH).

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACADIA Pharmaceuticals Inc.; ANDERSSON, Carl-Magnus A.; CROSTON, Glenn; HANSEN, Eva Louise; ULDAM, Allan Kjaersgaard; US2015/259291; (2015); A1;,
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A common heterocyclic compound, 16532-79-9, name is 4-Bromophenylacetonitrile, molecular formula is C8H6BrN, 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. 16532-79-9.

To a solution of (4-bromo-phenyl)-acetonitrile (1 g, 5.10 mmol) in DMF (10 mL) is added sodium hydride (0.408 g, 10.20 mmol, 60% in mineral oil) at 0 C. Thereaction mixture is stirred at 0 C for 15 minutes and then methyl iodide (0.69 mL, 11.22 mmol) is added at 0 C. The reaction mixture is stirred at room temperature forovernight. The reaction mixture is quenched with aqueous ammonium chloride solution (5 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts arewashed with water (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, filtered, and evaporated. The crude material is purified over silica gel column chromatography(combiflash) eluting with 5-10% EtOAc in hexanes to give an off white solid (0.9 g,78%). 1H NMR (400 MHz, CDC13) i5 7.51 (d, J = 8.4 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H),1.77 (s, 3H).

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

Reference:
Patent; ELI LILLY AND COMPANY; HAMDOUCHI, Chafiq; MAITI, Pranab; MILLER, Anne Reifel; WO2015/105779; (2015); A1;,
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