Month: August 2021

Application of 1187-42-4, 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. 1187-42-4, name is Diaminomaleonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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Application of 114897-91-5, 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 114897-91-5 as follows.

Step (2) Preparation of N’-Hydroxy-2-(4-bromo-2-fluorophenyl)ethanimidamide Hydroxylamine hydrochloride (8.93 g, 128.5 mmol), was added in one portion to a solution of sodium methoxide, freshly prepared from sodium (2.96 g, 128.5 mmol) in methanol (200 mL). The resulting mixture was stirred 1 hour at room temperature, during which a precipitate was formed. 4-Bromo-2-fluorophenylacetonitrile (11.0 g, 51.4 mmol) was added and the resulting mixture heated to reflux for 20 hours. A white solid was removed by filtration of the hot mixture and discarded. The filtrate was concentrated to a volume of 100 mL to give a precipitate which was washed with water, followed by 5% EtOAc/hexanes. A second crop was obtained from the filtrate upon further concentration. The two crops were combined and dried in vacuo to give the product as a white crystalline solid (10.4 g, 82%) of sufficient purity for use in the subsequent reaction. NMR (DMSO-d6): delta 8.99 (s, 1H), 7.44 (dd, J1 =9.2 Hz, J2 =1.3 Hz, 1H), 7.32 (m, 2H), 5.47 (br s, 2H), 3.30 (s, 2H).

According to the analysis of related databases, 114897-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corp.; US4895862; (1990); A;,
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Nitriles – Chemistry LibreTexts

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. 6621-59-6, name is 6-Bromohexanenitrile, A new synthetic method of this compound is introduced below., Safety of 6-Bromohexanenitrile

To a solution of 3-(1H-indol-3-yl)-4-(1-methyl-1H-indol-3-yl)furan-2,5-dione 39 (0.505?g, 1.48?mmol) in anhydrous DMF (20?mL) under nitrogen was added sodium hydride (60?wt% oil dispersion, 0.070?g, 1.77?mmol) and the mixture was stirred for 40?min at room temperature. 6-Bromohexane nitrile (0.30?mL, 0.38?g, 2.2?mmol) was then added and the reaction was stirred for a further 16?h. Water (40?mL) was then added and the mixture was extracted with ethyl acetate (3?*?30?mL). The combined organic layers were then washed with 1?M aqueous HCl (2?*?30?mL), followed by water (30?mL) and brine (30?mL) before being dried over anhydrous magnesium sulfate, filtered and the solvent evaporated under reduced pressure. The crude residue was purified using column chromatography on silica gel with 30% ethyl acetate/hexane to give desired product as a red solid (0.258?g, 40%): m.p. 78-79?C; numax/cm-1 (KBr) 3411, 2936, 2244, 1816, 1750, 1529, 1254, 1100, 741; deltaH (400?MHz, DMSO-d6) 1.27-1.35 [2H, m, C(4″)-H2], 1.56 [2H, quin, J 7.4, C(3″)-H2], 1.73 [2H, quin, J 7.4, C(5″)-H2], 2.44 [2H, t, J 6.9, C(2″)-H2], 3.89 (3H, s, CH3), 4.24 [2H, t, J 6.9, C(6″)-H2], 6.69-6.72 [2H, m, C(6′, 7′)-H], 6.79 [1H, t, J 7.6, C(6)-H], 7.01 [1H, d, J 8.15, C(7)-H], 7.07-7.13 [2H, m, (5, 5′)-H], 7.49 [1H, d, J 8.15, C(4′)-H], 7.54 [1H, d, 8.49, C(4)-H], 7.82 [1H, s, C(2)-H], 7.97 [1H, s, C(2′)-H]; deltac (75?MHz, DMSO-d6) 16.0 (CH2), 24.3 (CH2), 25.1 (CH2), 28.7 (CH2), 33.0 (CH3), 45.6 (CH2), 103.9 (C, aromatic C), 104.3 (C, aromatic C), 110.50 (CH, aromatic CH), 110.54 (CH, aromatic CH), 120.0 (CH, aromatic CH), 120.1 (CH, aromatic CH), 120.5 (CN), 121.4 (CH, aromatic CH), 121.5 (CH, aromatic CH), 122.1 (CH, aromatic CH), 122.2 (CH, aromatic CH), 125.0 (C, aromatic C), 125.7 (C, aromatic C), 127.0 (C, aromatic C), 127.9 (C, aromatic C), 132.9 (CH, aromatic CH), 134.3 (CH, aromatic CH), 135.9 (C, aromatic C), 136.7 (C, aromatic C), 166.3 (C=O), 166.5 (C=O); m/z (ESI+) 438.2 [(M+H)+ 12%]; HRMS (ESI+): Exact mass calculated for (C27H24N3O3)+ 438.1818. ;Found 438.1802.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Winfield, Hannah J.; Cahill, Michael M.; O’Shea, Kevin D.; Pierce, Larry T.; Robert, Thomas; Ruchaud, Sandrine; Bach, Stephane; Marchand, Pascal; McCarthy, Florence O.; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4209 – 4224;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 4421-09-4,Some common heterocyclic compound, 4421-09-4, name is 3,4-(Methylenedioxy)benzonitrile, molecular formula is C8H5NO2, 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.

DIPEA (12.17 ml, 69.7 mmol) was added to a suspension of piperonylonitrile (5 g, 34.0 mmol) and hydroxylamine hydrochloride (4.72 g, 68.0 mmol) in EtOH (75 mL). After stirring at 20 C. for 21.5 h, the reaction mixture was concentrated to dryness. The resulting colorless oil was cooled to 0 C. and cold water was added (75.0 mL) and the mixture was stirred for 30 minutes to give a white slurry. The solids were filtered, washed with water (2×15 mL) and the resulting solid dried at 40 C. under high vacuum until constant weight to afford Intermediate 6a (Z)-N?-hydroxybenzo[d][1,3]dioxole-5-carboximidamide (5.76 g, 94% yield) as a white solid: 1H NMR (DMSO-d6) is consistent with the desired product; MS m/z 181.1 (MH+); HPLC 100%, Rt=0.16 (0.31) min. Alternatively DIPEA can be replaced by sodium carbonate or commercial sodium ethoxide while working in ethanol as solvent for the reaction. Except when commercially available, all N?-hydroxycarboximidamides cited in the examples hereafter were prepared following the recipe outline before for intermediate 6a with the appropriate nitrile precursor and including its variation on the nature of the base used.

The synthetic route of 4421-09-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lamarre, Daniel; US2015/133495; (2015); A1;,
Nitrile – Wikipedia,
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Synthetic Route of 58633-04-8, 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 58633-04-8 as follows.

EXAMPLE 2 Preparation of 3,5-Dibromobenzonitrile STR16 To a stirred solution of t-butylnitrite (53.5 muL, 0.449 mmoles) in 1 ml sieve dried dimethylformamide at 50 C. under an atmosphere of nitrogen was added a solution of 4-amino-3,5-dibromobenzonitrile (50 mg, 0.179 mmoles) in 1 mL of DMF. The mixture was stirred at 50 C. for 0.5 hour and partitioned between diethyl ether, ice-water, and ammonium chloride. The organic phase was separated, washed with water and brine, dried over anhydrous sodium, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (9:1) as eluant provided 28 mg (59%) of white, crystalline product. NMR(CDCl3) delta: 7.7 (d, J=1.8Hz, 2H), 7.9 (t, J=1.8Hz, 1H).

According to the analysis of related databases, 58633-04-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc.; US5192758; (1993); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 38487-86-4, name is 2-Amino-4-chlorobenzonitrile, 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 38487-86-4, COA of Formula: C7H5ClN2

Step 1 2-Amino-4,5-dichlorobenzonitrile A 10 mL round bottom flask was charged with 2-amino-4-chlorobenzonitrile (0.2 g, 1.31 mmol), N-chlorosuccinimide (0.19 g, 1.44 mmol) and DMF (5 mL). The resulting mixture was stirred at 25 C. overnight. Reaction progress was monitored by TLC (EtOAc/Petroleum ether=1:10). Work-up: the reaction mixture was diluted with EtOAc (40 mL) and washed with brine (40 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a 1:10 EtOAc/Petroleum ether, to afford 170 mg (47%) of the product as white solid. 1H NMR (300 MHz, CDCl3) delta: 7.45 (s, 1H), 6.88 (s, 1H), 4.48 (br, 2H).

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, 2-Amino-4-chlorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kalypsys, Inc.; Alcon Research, Ltd; US2010/120741; (2010); A1;,
Nitrile – Wikipedia,
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Electric Literature of 34403-48-0, The chemical industry reduces the impact on the environment during synthesis 34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, I believe this compound will play a more active role in future production and life.

Et3N (35.96 ml, 256 mmol) was added to a solution of the amine (31.17 g, 213 mmol) in CH2Cl2 (150 ml). Benzyl chloroformate (36.37 ml, 256 mmol) in CH2Cl2 (50 ml) was then added dropwise at a temperature of 0 C. The reaction mixture was stirred overnight at RT and washed with aqueous 0.1 M HCl (150 ml) and H2O (150 ml), dried over Na2SO4 and filtered out, and the solvent was removed in vacuo.

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-((Methylamino)methyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; US2008/153843; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 2698-41-1, name is 2-(2-Chlorobenzylidene)malononitrile, molecular formula is C10H5ClN2, 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: 2698-41-1

General procedure: To a stirred mixture of aromatic aldehyde (2.0 mmol) and malononitrile (2.0 mmol) in ethanol (10 ml), a catalytic amount of DMA (5 mol%) was added at room temperature. To the precipitated solid materials, ethanolic solution of dimedone orethyl acetoacetate or barbituric acid (2.0 mmol) was added and from the resultingsolution, the products get precipitated within the time mentioned in Tables 1, 2, 3,and 4. For 4H-benzo[h]chromenes, 1-naphthol (2.0 mmol) was added to the arylidenemalononitrile and stirred at 70 C until the solid appeared. The productswere filtered, air-dried, and recrystallized from ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2698-41-1, its application will become more common.

Reference:
Article; Ramesh, Rathinam; Lalitha, Appaswami; Research on Chemical Intermediates; vol. 41; 10; (2015); p. 8009 – 8017;,
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Application of 53312-80-4, 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. 53312-80-4 name is 4-Amino-2-fluorobenzonitrile, 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.

Sodium cyanide (0.74 g, 15 mmol) was added to a mixture of 4-amino-2- fiuorobenzonitrile (1.36 g, 10 mmol) and cyclopentanone (1.26 g, 15 mmol) in 90% acetic acid (10 ml). The reaction mixture was stirred at room temperature for 3 hours and then the medium was hearted to 80 0C and stirred for an additional 5 hours. The medium was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 97:3) to yield 4-(l-cyanocyclopentylamino)-2-fluorobenzonitrile (54b) (2.07 g, 9.03 mmol, 90%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 1.69-1.91 (m, 4H), 2.13-2.18 (m, EPO 2H), 2.37-2.42 (m, 2H), 5.08 (bs, IH), 6.54-6.62 (m, 2H), 7.39 (t, J= 7.3 Hz, IH); 13C NMR (CDCl3, 100 MHz) delta 23.7, 39.8, 56.8, 89.6 (d, J = 15.8 Hz), 101.2 (d, J= 23.8 Hz), 110.9, 115.2, 120.8, 134.1 (d, /= 2.4 Hz), 150.3 (d, J= 11.2 Hz), 164.5 (d, J= 254.1 Hz).

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; WO2006/124118; (2006); A1;,
Nitrile – Wikipedia,
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Related Products of 1000339-52-5, 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. 1000339-52-5, name is 3-Fluoro-2-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of fluorine substituted 2-nitrobenzonitrile (18.06 mmol, 3 g) in DMF (50 mL) was added 1-Boc-piperazine (36.12 mmol, 6.727 g) and K2CO3 (18.06 mmol, 2.496 g), and the mixture solution was stirred for 5 h at 160 C. The mixture was extracted with DCM. The organic layer was separated and dried over Na2SO4. Removal of the solvent produced a residue which was purified using column chromatography, eluted with a mixture of MeOH:CH2Cl2 (1:30, v:v), to afford intermediate 7a-1, 7c-1.

The synthetic route of 3-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Wenwen; Wang, Huan; Li, Xiaokang; Xu, Yixiang; Zhang, Jian; Wang, Wei; Gong, Qi; Qiu, Xiaoxia; Zhu, Jin; Mao, Fei; Zhang, Haiyan; Li, Jian; Bioorganic and Medicinal Chemistry; vol. 26; 12; (2018); p. 3117 – 3125;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts