Tag: M.W=200-300

57381-44-9, name is 5-Bromo-2-chlorobenzonitrile, 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. HPLC of Formula: C7H3BrClN

3.1.1 2-chloro-5-piperazin-1-yl-benzonitrile (V-1) 0.200 g tert-butyl piperazine-1-carbamidate, 0.235 g 5-bromo-2-chlorbenzonitrile, 0.013 g tris(dibenzylideneacetone)dipalladium(0), 0.018 g rac-BINAP and 0.145 g sodium-tert-butoxide are suspended in 5 ml anhydrous, degassed toluene and heated under argon at 80 C until no further reaction takes place. The reaction mixture is filtered through Celite and mixed with a saturated sodium chloride solution. The product is extracted with ethyl acetate, dried and evaporated to dryness. 0.450 g tert-butyl 4-(4-chloro-3-cyanophenyl)-piperazine-1-carbamidate are obtained as an oil. The product obtained and 2 ml trifluoroacetic acid are suspended in 3 ml dichloromethane. The reaction mixture is stirred at ambient temperature until no further reaction takes place and then evaporated to dryness. The residue is suspended in diethyl ether and the solid is suction filtered. 0.300 g (V-1) are obtained as the trifluoroacetate. Analytical HPLC-MS (method B): RT=1.02 min

The synthetic route of 57381-44-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/28441; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 2112-22-3,Some common heterocyclic compound, 2112-22-3, name is 2,3-Dichloro-6-nitrobenzonitrile, molecular formula is C7H2Cl2N2O2, 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.

2,3-dichloro-6-nitrobenzonitrile, 500 gm, was dissolved in 7500 ml of THF in a clean dry RB flask maintaining a nitrogen blanket. 139.3 am of sodium borohydride was added at 25-30 C. The suspension was cooled to 15-20 C. 653 gms of Borontrifluoride etherate was added to the reaction mixture over a period of about 2 hours while maintaining the temperature between 15-30 C. After the addition was complete, the temperature was raised about 65 C. and maintained at reflux for 2 hours. The reaction mixture was cooled to about 0-5 C. A mixture of 2.0 liter water and 200 ml concentrated HCl was slowly added to the reaction mixture while maintaining the temperature below 20 C. After the addition was complete, THF was distilled from the reaction mixture under vacuum maintaining temperature below 50 C. The reaction mixture was cooled to about 10-15 C. and 2.0 liter ethylacetate was added. The pH of reaction mixture was adjusted to 10-11 using 25% aqueous sodium hydroxide solution while maintaining the temperature below 15 C. The ethylacetate layer was separated and concentrated to about half the original volume. The reaction mixture was cooled to 15-20 C. and 500 ml IPA-HC1 was added slowly, maintaining temperature below 30 C. After cooling to about 0-5 C., the solids obtained were filtered and washed with 500 ml chilled ethylacetate. The solids were dried to obtain 2,3-dichloro-6-nitrobenzyl amine hydrochloride (450 gms),

The synthetic route of 2112-22-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WATSON PHARMA PRIVATE LIMITED; US2010/305318; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

51655-39-1, name is 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile, 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. Quality Control of 2-(2-Bromo-4,5-dimethoxyphenyl)acetonitrile

Example 7 3-(ETHOXY-HYDROXY-METHYLENE)-5,6-DIMETHOXY-3H-INDENE-1-CARBONITRILE, SODIUM SALT A solution of tricyclohexylphosphine (82.0 mg, 0.293 mmol) in ethylene glycol dimethyl ether (10 mL) under nitrogen was charged with palladium (II) acetate (43.7 mg, 0.195 mmol). The reaction was stirred at room temperature until the solution was homogeneous (approx. 15 minutes) and stirred an additional 5 minutes before cooling to 0 C. and charging with sodium tert-butoxide (996 mg, 9.75 mmol). After 5 minutes a solution of 2-bromo-4,5-dimethoxyphenylacetonitrile (1.00 g, 3.90 mmol) and ethyl-3-ethoxyacrylate (0.564 ml, 3.90 mmol) in ethylene glycol dimethyl ether (5 ml) was added dropwise over 10 minutes. Upon complete addition the reaction mixture was warmed to room temperature and then heated to 85 C. for 16 hours. The reaction was cooled to room temperature then diluted with methyl tert-butyl ether (50 mL) and poured into aqueous potassium dihydrogenphosphate (0.25 M, 100 mL). The aqueous layer was separated and solid sodium chloride was added to the aqueous layer until saturated. The aqueous layer was extracted with ethyl acetate (1*125 mL) and this organic layer was washed with aqueous saturated sodium chloride 12*35 ml), dried over sodium sulfate, filtered and concentrated in vacuo affording 3-(ethoxy-hydroxy-methylene)-5,6-dimethoxy-3H-indene-1-carbonitrile, sodium salt, as a dark brown oil (906 mg, 3.3 mmol, 85 %) which crystallized on standing. 1H NMR (400 MHz, d4-MeOH) delta7.64 (s, 1H), 7.46 (s, 1H), 6.99 (s, 1H), 4.56 (q, 2H, J=7.1), 3.86 (s, 6H), 1.38 (t, 3H, J=7.05); 13C NMR (100 MHz,d4-MeOH) delta167.8, 145.0, 144.5, 130.2, 129.4, 126.4, 123.3, 112.5, 104.0, 102.6, 100.7, 79.0, 58.4, 55.6, 14.1; IR (ATR, neat) 3499, 2164, 1629, 1482, 1449, 1282, 1207, 1157, 1124, 1076, 845, 769 cm-1.

The synthetic route of 51655-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Singer, Robert A.; US2003/60624; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 129931-47-1, 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. 129931-47-1 name is 3-Chloro-2-fluoro-5-(trifluoromethyl)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.

(g) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-trifluoromethyl-2-pyridone (Compound No 14 of Table II) was prepared by reacting 3-chloro-4-fluoro-5-cyanotrifluoromethylbenzene and 4-trifluoromethyl-2-pyridone. 1 H NMR delta(CDCl3) 8.10 (1H,d); 8.0 (1H,d); 7.26 (1H,dd); 7.04 (1H,s); 6.55 (1H,dd).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 2286-54-6, A common heterocyclic compound, 2286-54-6, name is 3,3-Diphenylpropanenitrile, molecular formula is C15H13N, 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.

In the glove box, 0.01 mmol of nickel chloride was added, 0.52 mmol of diphenylphosphine oxide, 1.5 equivalents of t-BuOK (potassium tert-butoxide),Add to the Schlenk reaction tube in turn, then Add 0.4mmol 1, 1-diphenylpropionitrile compound, Vacuum and backfill nitrogen; under a nitrogen atmosphere, add 3 ml of 1,4-dioxane to the solvent. The reaction was continued at 120 C for 16 h. After the reaction is completed, it is cooled to room temperature and separated by column chromatography. That is the target product: 1,1-diphenylethyldiphenylphosphine oxide, yield 87%.

The synthetic route of 2286-54-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University; Zhang Jishu; Qi Tafamingrenqingqiubugongkaixingming; (13 pag.)CN109438512; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 133541-45-4, 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. 133541-45-4 name is 4-Bromo-2,5-difluorobenzonitrile, 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.

A mixture of 100 mg (0.46 mmol) 4-bromo-2,5-difluoro-benzonitrile, 146 mg (0.78 mmol) intermediate 111.14, 0.2 ml (1 .42 mmol) DIPEA and DMSO is heated to 100C for 5.5 h. After cooling to RT the reaction mixture is diluted with ACN and water and purified by HPLC giving rise to 1 16 mg 4-bromo-2-[4-(4-cyanophenyl)piperazin-1 -yl]- 5-fluoro-benzonitrile

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,5-difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HIMMELSBACH, Frank; BLUM, Andreas; PETERS, Stefan; (80 pag.)WO2017/148518; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 76574-39-5, 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. 76574-39-5, name is 2-(2-Bromo-6-chlorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(2-Bromo-.6-chlorophenyl)acetonitrile (450 mg, 2.0 mmol) (43-1), 3- pyridylboronic acid (251 mg, 2.1 mmol) (43-2), potassium fluoride (230 mg, 3.9 inmol), 1,4- dioxane (12 mL), methanol (3.6 rnL), Pd2(dba)3 (71 rng, 0.080 mrnol) and dicyciohexyl-12-(2,6- dimethoxyphenyl)phenyi]phosphane (32 Ing, 0.080 mmol) were combined under an atmosphere of nitrogen and the resulting mixture was heated at 80 C After 16 h, the reaction was filtered and concentrated under reduced pressure. The resulting oil was dissolved in DCM and purified by silica gel chromatography eluting with methanol/dichloromethane to afford 317 mg (71%) 2- [2.-chloro-6-(-pyridyl)phenyllacetonitriie (43-3). LCMS (ESI): [M+Hf = 229.1

The synthetic route of 2-(2-Bromo-6-chlorophenyl)acetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 77429-04-0, name is Ethyl 3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate, 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 77429-04-0, HPLC of Formula: C7H5ClF3NO2

To a mixture of 21 g of ethyl 3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate and 7.6 g of 4- nitrobenzimidamide in 300 ml of water, 31 ml of a aqueous sodium hydroxide solution (2M) were added. The reaction mixture was stirred at RT for 4 h, then diluted with 200 ml of water, acidified with half-concentrated aqueous hydrochloric acid to pH 3 and extracted with EtOAc (3 x 500 ml). The combined organic layers were dried over magnesium sulfate and the solvents were removed under reduced pressure. The crude product was purified by chromatography on silica gel eluting with a gradient of EtOAc/methanol. Yield: 2.7 g.

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.

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. 2286-54-6, name is 3,3-Diphenylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3,3-Diphenylpropanenitrile

A solution of hydroxylamine hydrochloride (38.6 ml, 38.6 mmol) in MeOH was added to a solution of potassium hydroxide (38.6 ml, 38.6 mmol, Eq: 4) in MeOH at 0 C. The resulting mixture was filtered and the filtrate was added to a 150 mL round-bottomed flask containing 3,3-diphenylpropanenitrile (2 g, 9.65 mmol). The mixture was heated at reflux for 16 h, cooled and evaporated to dryness. The residue was dissolved in EtOAc, washed with brine, dried (MgSO4) and evaporated to dryness. The crude product was dissolved in CHCl3 (50 ml), treated with dimethyl but-2-ynedioate (1.65 g, 11.6 mmol, Eq: 1.2) and heated at reflux for 1 h and then evaporated to dryness. The residue was dissolved in xylene (10 ml), heated at 120 C. in a microwave oven for 4 h and evaporated to dryness. Chromatography (80 g SiO2; 20 to 100% EtOAc in hexanes) gave the title product as an off-white solid (0.42; 12%). LCMS: m/z=348.9 (MH+).

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 2286-54-6.

27387-23-1, name is 2-(2-Bromo-5-methoxyphenyl)acetonitrile, 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. Quality Control of 2-(2-Bromo-5-methoxyphenyl)acetonitrile

To a solution of s2 in EtOH (10.0 mL) and H2O (5.0 mL) were successively added NaOH (2.94 g,73.5 mmol) and aqueous H2O2 (23 muL, 0.736 mmol) at room temperature. After the mixture washeated to reflux for 24 h, the reaction was quenched by addition of conc. HCl at 0 C. The crudemixture was extracted with EtOAc (x4) and the combined organic extracts were washed with brine,dried (Na2SO4), and concentrated in vacuo to give crude s3 (1.62 g) as pale yellow solid. Thiscrude material was used for next reaction without further purification.

The synthetic route of 27387-23-1 has been constantly updated, and we look forward to future research findings.