Month: February 2021

Application of 7357-70-2, A common heterocyclic compound, 7357-70-2, name is 2-Cyanothioacetamide, molecular formula is C3H4N2S, 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.

10 g (58.74 mmol) of 2-(di(methylthio))methylidenemalononitrile and 7.1 g (70.48 mmol) of cyanothioacetamide were initially charged in 21 ml of DMF, and 16.4 ml (117.47 mmol) of triethylamine were added dropwise at room temperature. The mixture was stirred at room temperature for 8 h. The reaction mixture was added to 300 ml of 3N hydrochloric acid. The resulting precipitate was filtered off with suction, washed with water and dried. This gave the product as a powder.Yield: 12.2 g (89% of theory, 96% pure)1H-NMR (400 MHz, CDCl3): delta=3.98 (s, 1H), 2.72 (s, 3H).LC-MS (Method 7): Rt=1.56 min; MS (ESIpos): m/z=223 [M+H]+.

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nell, Peter; Vakalopoulos, Alexandros; Suessmeier, Frank; Albrecht-Kuepper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Meibom, Daniel; US2011/3845; (2011); A1;,
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Related Products of 50594-78-0, 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. 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of methyl 5-hydroxy-2-[(4-methylphenyl)sulfonyl]aminobenzoate (252 mg, 0.785 mmol), 4-fluoro-2-cyanonitrobenzene (137 mg, 0.825 mmol), and potassium carbonate (271 mg, 1.96 mmol) in DMF (5 mL) was stirred at 80 C. for 2.5 hours. The reaction was diluted with EtOAc (40 mL) and washed with aq. 0.5 N KHSO4 (1¡Á40 mL) and aq. saturated NaHCO3 (1¡Á40 mL). The water layers were extracted once more with EtOAc (40 mL). The combined EtOAc-layers were dried (Na2SO4), filtered, and evaporated to dryness in vacuo. The crude product was purified by flash column chromatography (EtOAc/heptane: 1/3 to 1/1) to obtain the desired product as yellow solid (292 mg, 79%, purity (LC)=85%).MS: [M-H]-=466

The synthetic route of 5-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dams, Gery Karel Julia; Vereycken, Inge; Van Acker, Koenraad Lodewijk August; Gustin, Emmanuel Marie Paul Ernest; Verschueren, Wim Gaston; Ohagen, Asa Catrine; US2010/280268; (2010); A1;,
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Related Products of 51762-67-5, 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. 51762-67-5, name is 3-Nitrophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of compound 1 (1.73 g, 7.29 mol) and 3-nitrophthalonitrile (1.26 g, 7.28 mol) in DMSO (30 mL) was stirred at room temperature for 10 min, and K2CO3 (2.52 g, 1.82 mol) was added with further stirring for 24 h. The reaction mixture was poured into 200 mL ice-water to give a great deal of yellow precipitate, which was collected by filtration and then washed with water. After dryness in vacuo, the product was obtained as a yellow solid (2.04 g, 94%). 1 H NMR (400 MHz, acetone-d6, ppm): d 7.85 (t, J 8.2 Hz, 1 H), 7.75 (d, J 7.6 Hz, 1 H), 7.40 (d, J 8.2 Hz, 2 H), 7.26 (d, J 8.7 Hz, 1 H), 7.19 (d, J 8.2 Hz, 2 H), 3.34 (t, J 7.0 Hz, 2 H), 2.86 (t, J 7.2 Hz), 1.40 (s, 9 H). MS (ESI): m/z 386.12 [M Na].

The chemical industry reduces the impact on the environment during synthesis 3-Nitrophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Peng, Xiao-Hui; Chen, Shao-Fang; Zheng, Bi-Yuan; Zheng, Bing-De; Zheng, Qiao-Feng; Li, Xing-Shu; Ke, Mei-Rong; Huang, Jian-Dong; Tetrahedron; vol. 73; 4; (2017); p. 378 – 384;,
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Related Products of 53312-81-5, 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 9: 5- 5-(Benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrileA suspension of 2-chloro-5-benzyloxypyrimidine (2.0g, 9.074mmol), 5-amino-2- fluorobenzonitrile (1.24g, 9.074mmol), in’5,(dibenzylideneacetone)palladium(0) (415 mg, 0.45mmol), 4,5-bi5,(diphenylphosphino)-9,9-dimethylxanthene (525 mg, 0.90 mol) and cesium carbonate (5.9g, 18.1mmol) in de-gassed 1,4-dioxane (15mL) was heated at 80 C for 2 days. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried (MgS04) and the solvent removed under reduced pressure. The crude product was purified by flash chromatography, using 0-5% ethyl acetate:hexane as eluent, to give 5- [5- (benzyloxy)pyrimidin-2-ylamino]-2-fluoro-benzonitrile (2.88g) as yellow solid.Mass: (ES+) 321(M+H)+

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SENEXIS LIMITED; HORWELL, David; SCOPES, David; WO2011/144577; (2011); A1;,
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Electric Literature of 1129-35-7,Some common heterocyclic compound, 1129-35-7, name is Methyl 4-cyanobenzoate, molecular formula is C9H7NO2, 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 METHYL-4-CYANOBENZOATE (5.0 g, 0. 031 MOL) and diethyl dithiophosphate (11.5 g, 0.062 mol) in water (100 mL) was stirred overnight at 80C under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperatures and the solid was filtered and washed with water (100 mL). The solid was then dried in vacuo at 40C to give the crude product (4.74 g, 78%).

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

Reference:
Patent; APPLIED RESEARCH SYSTEMS ARS HOLDING N.V.; WO2005/11685; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 79463-77-7, name is Diphenyl N-cyanocarbonimidate, belongs to nitriles-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 79463-77-7, category: nitriles-buliding-blocks

[00606] 147A. l-(3-Chloro-2-fiuorophenyl)-N-[(10R,14S)-5-{[(lZ)- (cyanoimino)(phenoxy)methyl] amino } – 10-methyl-9-oxo-8 , 16- diazatricyclo[13.3.1.02’7]nonadeca-l(19),2(7),3,5,15,17-hexaen-14-yl]-5-methyl-lH- l,2,3-triazole-4-carboxamide: A mixture of Example 89 (Alternative, HC1 salt) (10 mg, 0.016 mmol), pyridine (10.42 mu?, 0.129 mmol) and diphenyl cyanocarbonimidate (7.67 mg, 0.032 mmol) in 2-propanol (0.15 mL) was stirred in a pressure-tested vial at room temperature for 2 h. The reaction mixture was concentrated to give the product (11 mg, 99%) as an oily solid. MS(ESI) m/z: 692 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diphenyl N-cyanocarbonimidate, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
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Related Products of 194853-86-6, The chemical industry reduces the impact on the environment during synthesis 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

D. 4-Fluoro-3-iodo-2-(trifluoromethyl)benzonitrile To a freshly prepared solution of LDA (1 19 mmol) in anhyd THF (250 mL) at -45C is added a solution of commercially available 4-fluoro-2-(trifluoromethyl)benzonitrile (21 .5 g, 1 14 mmol) in THF (30 mL), dropwise at a rate such that the internal temperature remained < -40C (became dark brown during addition). The mixture is stirred 30 min at -45C, cooled to -70C and iodine (31 .7 g, 125 mmol) is added in one portion (-70C? - 52C). The mixture is stirred for 1 h, removed from the cooling bath and quenched by addition of 10% Na2S203 (ca. 250 mL) and 1 N HCI (ca. 125 mL). The mixture is extracted with EtOAc (x3). Combined organics are washed (water, brine), dried over Na2S04 and concentrated in vacuo. The residue is purified by low pressure liquid chromatography (silica gel, EtOAc / hexanes, gradient elution) followed by recrystallization from heptane (30 mL), twice, affording 4-fluoro-3-iodo-2- (trifluoromethyl)benzonitrile (15.79 g, 50.1 mmol, 44.1 % yield) as a pale yellow solid. 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-Fluoro-2-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KALDOR, Istvan; TANG, Dalin; WO2015/110958; (2015); 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 75279-53-7 as follows. COA of Formula: C8H5ClFN

A solution of 4-chloro-2-fluorobenzeneacetonitrile (0.059 mol) in anhydrous DMF (150 ml) was chilled on an ice-bath. t-BuOK (0.118 mol) was added under nitrogen and the resulting mixture was stirred for 30 minutes. l,2-Dichloro-4-methyl-5- nitrobenzene (0.059 mol) was added and the reaction mixture was stirred for 1 hour at 00C. The mixture was allowed to warm to room temperature for 1 hour and then cooled to 00C. A solution of hydrogen peroxide in water (30%) (17.8 ml) was added and air was bubbled through the solution overnight. The obtained mixture was slowly added dropwise to IN HCl (750 ml) and after stirring in ice-cold DIPE, the resulting precipitate was filtered off, yielding 5.83 g of intermediate (1).

According to the analysis of related databases, 75279-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; WO2008/152081; (2008); A2;,
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Related Products of 950596-58-4, 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. 950596-58-4 name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, 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.

In the reaction flask was charged with 2-amino-4,5-bis (2-methoxyethoxy) – benzonitrile (37.01g, 0.139mol) and acetonitrile (185ml); added 3-ethynyl aniline salt acid (30.00g, 0.195mol), trifluoroacetic acid (17.43g, 0.152mol) and formamidine acetate (15.19g, 0.145mol) in the resultant mixture.The reaction mixture temperature was adjusted to reflux temperature of the solvent, and maintained in this condition for about 15 hours.At the end of the reaction, the temperature was adjusted to about 25 , the solvent was removed by vacuum distillation, and methyl ethyl ketone (430ml).(2 ¡Á 100ml) and water (2 ¡Á 100ml) the organic phase was washed with saturated sodium bicarbonate solution.The organic phase was collected and concentrated by vacuum distillation to a residue.The resulting crude product was suspended in ethyl acetate (450ml), and adding 37% hydrochloric acid solution (14.38g, 0.145mol), maintained at a temperature of 15 for about 30 minutes.The resulting solid was filtered, washed under vacuum at 45 C oven dried to obtain 36.02g erlotinib hydrochloride.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Guilin Hui Pak Biotechnology Co., Ltd.; M, Balatella; P, Palanza; M, Garbodi; G, Castaldi; (7 pag.)CN105541735; (2016); A;,
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Application of 6011-14-9,Some common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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-aminoacetonitrile hydrochloride (5 g, 54.0 mmol), NaHC03(18.16 g, 216 mmol) and dioxane (50 mL) in H20 (100 mL) was stirred at 0C. Then a solution of benzyl carbonochloridate (1 1.06 g, 64.8 mmol, 9.22 mL) in toluene (10 mL) was added at 0C and stirred at 20C for 12 hours. The mixture was poured into water (100 mL), and the aqueous phase was extracted with ethyl acetate (100 mLchi3).The combined organic phases were washed with brine (100 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to give benzyl(cyanomethyl)carbamate (1 .70 g).1H NMR (chloroform-c/400 MHz): 7.40-7.31 (m, 5H), 5.35- 5.13 (m, 3H), 4.16-4.12 (m, 2H).

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

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (270 pag.)WO2018/7249; (2018); A1;,
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