Category: nitriles-buliding-blocks

Reference of 501420-63-9,Some common heterocyclic compound, 501420-63-9, name is 2-(3-Bromo-4-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

(3-Bromo-4-fluorophenyl)acetonitrile (4.00 g, 18.32 mmol), bis(pinacolato)diboron (5.22 g, 20.15 mmol), potassium acetate (55.86 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.2% of Pd) (393.53 mg, 0.55 mmol) were dissolved in oxygen-free 1,4-dioxane (40 ml, max. 0.005% of water) under argon. The reaction mixture was subsequently heated at a temperature of 130 C. for 90 min. When the reaction conversion was complete, the mixture was filtered through kieselguhr. The filtrate was diluted with dichloromethane (200 ml) and water (50 ml) and extracted. The organic phase was dried over sodium sulfate, subsequently filtered and evaporated to dryness in vacuo, giving [4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile as oil (7.59 g, purity 81%, MS: 262.2 [M+H+]), which was reacted further without further work-up.

The synthetic route of 501420-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; FUCHSS, Thomas; EMDE, Ulrich; BUCHSTALLER, Hans-Peter; MEDERSKI, Werner; (224 pag.)US2016/83401; (2016); A1;,
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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. 115661-37-5, name is 2-Amino-3-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 115661-37-5

To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) over 10 min at 0C. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
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17983-30-1, name is 3-Oxocyclohexanecarbonitrile, belongs to nitriles-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. Safety of 3-Oxocyclohexanecarbonitrile

Example 2Conversion of 3-cyanocyclohexanone to 3-aminomethyl-1-cyclohexylamineThe apparatus used consisted of 8 tubular reactors connected in series. The dimensions of the first two tubes (C1-C2) were 1500¡Á6¡Á1 mm. The dimensions of the 6 further tubes (C3-C8) were 2000¡Á8¡Á1.5 mm. The first two reactors (C1-C2) were charged with 15.7 g of TiO2 extrudates with a diameter of 1.5 mm, the remaining 6 reactors each with approx. 85 g of a hydrogenation catalyst (Mn3O4 5-6.2%, Na2O 0-0.5%, H3PO4 2.8-3.8%, remainder Co+CoO) which had been reduced with hydrogen at 280 C. at a pressure of 1 bar for 24 hours.The temperature of the first two reactors C1-C2 was adjusted to 60 C. The temperature of reactors C3-C4 was 90 C., the temperature of reactors C5-C6 was 115 C. and the temperature of reactors C7-C8 was set to 130 C. Between reactors C2 and C3, hydrogen was fed into the reaction mixture under pressure. The operating pressure was 230 bar.23 g/h of a mixture of THF and 3-cyanocyclohexanone in a ratio of 1:1 together with 73 g/h of NH3 were pumped into the first reactor (C1), and 17 standard liters/h of hydrogen were also fed in upstream of reactor C3. The reaction output was decompressed through a regulating valve. In a downstream phase separator, hydrogen was then removed and ammonia was evaporated off.A total of 592 g of 3-cyanocyclohexanone were used. The crude output was distilled through a 60 cm column with random packing at <1 mbar. The product distilled over at 54 C. 433.7 g of 3-aminomethyl-1-cyclohexylamine were obtained as a mixture of cis/trans isomers with a purity of 99.5% (cis: 85.6, trans: 14.1; CT ratio: 86:14). The yield in the hydrogenation stage was 84% including the product content in the different fractions and 70.4% of pure product after the distillation.The mixture of the isomeric diamines was characterized by GC-MS, NMR and elemental analysis.13C-NMR (125 MHz, DMSO): 50.33 (cis-AMCHA), 48.57 (cis-AMCHA), 47.22 (trans-AMCHA), 45.35 (trans-AMCHA) 41.26 (cis-AMCHA), 40.43 (cis-AMCHA), 38.02 (trans-AMCHA), 36.88 (cis-AMCHA), 35.03 (trans-AMCHA), 34.53 (trans-AMCHA), 29.87 (cis-AMCHA), 29.44 (trans-AMCHA), 24.61 (cis-AMCHA), 19.66 (trans-AMCHA).In the GC-MS, by the method of 30m db35 MS 0.25 micrometer, start temperature 60 C., temperature ramp 5 C./min to 280 C. and bakeout at this temperature for 30 min, two main peaks were detected, retention times 19.07 min (85.6 area %) and 19.2 min (14.1 area %).The following fragment distributions were obtained (M+=128 corresponds to the particular molecular peak):Peak 1:m/z (%)=18(5), 27(5), 28(14), 29(7), 30(59), 39(9), 41(15), 42(13), 43(48), 44(17), 53(5), 54(12), 55(11), 56(100), 57(15), 58(9), 67(23), 68(11), 69(17), 70(18), 71(3), 77(4), 79(6), 80(3), 81(9), 82(28), 83(9), 85(4), 94(3), 96(8), 98(79), 99(36), 110(6), 111(19), 112(3)Peak 2:m/z (%)=18(4), 27(6), 28(14), 29(7), 30(61), 39(10), 41(16), 42(15), 43(45), 44(12), 53(6), 54(11), 55(11), 56(100), 57(32), 58(9), 67(20), 68(11), 69(20), 70(18), 71(3), 77(4), 79(7), 80(3), 81(9), 82(25), 83(14), 84(3), 85(3), 94(3), 96(10), 98(68), 99(22), 110(7), 111(41), 112(5)To determine the elemental analyses, an Elementar Vario EI III automatic analyzer was used.The elemental analysis gave_C=64.8 (expected: 65.6); N=22.1 (expected: 21.9); H=12.8 (expected: 12.6) g/100 g The synthetic route of 17983-30-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASF SE; US2011/124919; (2011); A1;,
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Reference of 874-97-5, 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. 874-97-5, name is 3-Cyanobenzyl alcohol belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure 2: In a vial the acid (1.32 mmol), dicyclohexylcarbodiimide (DCC; 1.45 mmol) and the alcohol (1.32 mmol) were dissolved in dry THF (5mL). The reaction mixture was stirred at room temperature overnight, and then filtered. The filtrate was diluted with dichloromethane and washed with water (2x) followed by brine, dried over sodium sulfate and concentrated to a crude residue, which was purified by flash chromatography.

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-Cyanobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Titchenell, Paul M.; Hollis Showalter; Pons, Jean-Francois; Barber, Alistair J.; Jin, Yafei; Antonetti, David A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 3034 – 3038;,
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Reference of 103146-25-4, 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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

In a 200-ml four-necked flask equipped with a stirrer and a thermometer, 1.5 g [(4.] [38] m mol) of [()-4- [4-DIMETHYLAMINO-1- (4′-FLUOROPHENYL)-1-HYDROXYBUTYL]-3-] hydroxymethylbenzonitrile was dissolved in 30 ml of toluene, then 0.45 g of Novozym 435 (product [OF NOVOZYMES),] 0.347 g (4.38 m mol) of pyridine, 4.38 m mol of various kinds of acids and 1.00 g (8.76 m mol) of vinyl butyrate were added, and stirred at [40C] for between 16 and 21.5 hours. The result is shown in Table 4.

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, 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. LUNDBECK A/S; WO2004/14821; (2004); A1;,
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147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, belongs to nitriles-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. Recommanded Product: 4-Fluoro-2-methylbenzonitrile

Preparation 7; 2-(bromomethyl)-4-fluorobenzonitrile; A solution of 2-methyl-4-fluoro-benzonitrile (3.5 g, 25.9mmol) in 4OmL of carbon tetrachloride was treated with N-bromosuccinimide (4.6g, 25.9 mmol) and benzoylperoxide (157mg, 0.65 mmol). The mixture was heated to reflux for 3 hours, cooled to room temperature and allowed to stir overnight. The solids were filtered off and washed with carbon tetrachloride. The filtrate was condensed and purified by normal phase flash column chromatography on a 50 g silica gel column (5 – 50percent ethyl acetate/hexanes gradient). Two peaks separated. It was determined that the second eluting peak is the desired product. Pure fractions of this peak were pooled and concentrated in vacuo to yield 2-(bromomethyl)-4- fluorobenzonitrile (1.35g, 0.63 mmol, 25percent yield) as a white solid. 1H NMR (400 MHz, DMSO-dbeta) delta ppm 4.79 (s, 2 H), 7.44 (dt, J=8.59, 2.69 Hz, 1 H), 7.68 (dd, J=9.53, 2.55 Hz, 1 H), 8.01 (dd, J=8.59, 5.64 Hz, 1 H).

The synthetic route of 147754-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2008/53300; (2008); A1;,
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Synthetic Route of 75344-77-3, A common heterocyclic compound, 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile, molecular formula is C9H8BrN, 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.

3-(4-Bromo-3,5-dimethyl-phenyl)-1H-tetrazole 4-Bromo-3,5-dimethyl benzonitrile (3.0 g, 14.3 mmol), sodium azide (2.32 g, 35.7 mmol) and ammonium chloride (2.3 g, 42.84 mmol) are suspended in dry N,N-dimethylformamide and heated at 140 C. for 7 hours. The mixture is allowed to cool to room temperature, diluted with water and the precipitated solid collected by filtration, washed with water and dried to give the title compound (yield 1.74 g). The mother liquor was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic extracts were combined and the solvent removed to give a second crop of title compound (yield 1.39 g, total yield 3.13 g). LC (MIL-07-002): tR=0.83 min; Mass spectrum (ES+): m/z=253/255 [M+H]+.

The synthetic route of 75344-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HAMPRECHT, Dieter; FRATTINI, Sara; LINGARD, Iain; PETERS, Stefan; US2013/324514; (2013); A1;,
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These common heterocyclic compound, 6136-93-2, name is 2,2-Diethoxyacetonitrile, 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. Recommanded Product: 2,2-Diethoxyacetonitrile

To a vial was added 2,2-diethoxyacetonitrile (XIX) (1.0 g, 7.74 mmol) dissolved MeOH (7.74 mL) followed by addition of MeONa/MeOH (0.18 mL, 0.77 mmol) dropwise. The reaction was stirred at room temperature for 20 h. HOAc (44.3 muL, 0.77 mmol) was added until pH=7-8 (using pH strips). (4-Bromo-3-fluoro-phenyl)methanamine hydrochloride (XX) (1.86 g, 7.74 mmol) was added and stirred at 40 C. for 4 h. The solvent was removed under vacuum. Sulfuric acid (12.6 mL, 232.3 mmol) was added and stirred at 40 C. for 16 h. NH4OH (30.8 mL, 240.0 mmol) was added dropwise at 0 C. The solvent was removed under vacuum and the residue was purified by C18 silica gel (240 g) [0?50% H2O/MeCN (0.1% Formic acid)] to produce 6-bromo-7-fluoro-isoquinolin-3-amine (XXI) (1.33 g, 5.50 mmol, 71.1% yield) as an off-white solid. 1H NMR (499 MHz, DMSO-d6) delta ppm 6.07 (2H, s), 6.61 (1H, s), 7.76 (1H, d, J=9.33 Hz), 8.01 (1H, d, J=6.86 Hz), 8.80 (1H, s); ESIMS found for C9H6BrFN2 m/z 242.9 (81BrM+H).

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

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Hofilena, Brian Joseph; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; (149 pag.)US2019/125740; (2019); A1;,
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Related Products of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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.

Weighing 0.22 muM of sodium cyanide (2.2 equiv) in 250 ml three-neck bottle in, under ice bath by adding 110 ml THF, then adding 0.1 muM 1 a (1 equiv) and 0.1 muM 1 d (1 equiv), 65 C reflow 12 h. After the reaction, under the ice, with a certain amount of reaction water quenching, adjusting solution PH value to 4 – 5, ethyl acetate extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and get products 2 ad. 250 Ml three-neck bottle is added to the product of the 1st step 2 ad, 100 ml ethanol and 0.9 muM 2 g, 85 C reflow 18 h. Stopping the reaction, steaming and out ethanol, saturated sodium hydroxide solution to adjust the residue for the PH in 9 – 10. DCM extraction, the organic phase is dried with anhydrous sodium sulfate, and steaming and, column chromatography purification (dichloromethane: ethyl acetate=20:1) to obtain the product B3.

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

Reference:
Patent; China Agricultural University; Hou Shicong; Gao Gui; Chen Xiangzhu; Liu Jingjing; Zhang Yuanyuan; Zhang Xueyan; (10 pag.)CN107980784; (2018); A;,
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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 4435-14-7 as follows. HPLC of Formula: C8H13N

The isopropyl cyclohexylacetimidate hydrochloride used as the starting material was prepared as follows: In a manner analogous to that described in Example 1, from cyclohexylacetonitrile, there was obtained isopropyl cyclohexylacetimidate hydrochloride in the form of a pale pink solid of melting point 108-110 C.

According to the analysis of related databases, 4435-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US5399712; (1995); A;,
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