Tag: M.W=200-300

Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
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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. 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 2-cyano-4,4-diethoxybutyrate

2-Methyl-4-hydroxypyrrolo[2,3-d]pyrimidine (3).; Acetamidine hydrochloride (2, 0.05 mol, 4.7 g) was added to the 0.1 M sodium ethoxide solution (75 ml) and kept stirring under room temperature for 0.5 h. After removing the formed sodium chloride by filtration, the filtrate was added the ethyl alpha-cyano-gamma,gamma-diethoxybutyrate (1, 0.05 mol, 11.5 g) and the solution was heated under reflux for 5 h. After the removal of most solvent under vacuum, acetic acid was added to adjust the pH to 7.0 and 10.8 g precipitation as white powder. Ethanol (110 ml) with concentrated sulfuric acid (2 ml) was added to the collected powder and was refluxed for 2 h. By the end of the reaction an equal volume of water was added and kept at 4° C. overnight. The pyrrolopyrimidine 3 precipitated as white powder (2.1 g) was used for next step without further purification.

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:
Patent; Gangjee, Aleem; US2010/10016; (2010); A1;,
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Electric Literature of 32446-66-5, The chemical industry reduces the impact on the environment during synthesis 32446-66-5, name is 4,4′-Dicyanobenzophenone, I believe this compound will play a more active role in future production and life.

EXAMPLE 2; PREPARATION OF 4,4′-(HYDROXY METHYLENE)BISBENZONITRILE OF FORMULA IV 200 ml of methanol was taken into a round bottom flask followed by charging 40 g of 4,4-dicyanobenzophenone and stirring for about 10 minutes. 3.28 g of sodium borohydride was added slowly to the above suspension at 0-5 C. followed by stirring at 25-30 C. for 30 minutes, and the formed solution was neutralized with 25 ml of glacial acetic acid to a pH of 6.33. 800 ml of water was charged to the above-neutralized suspension and stirred for 30 minutes, and the precipitate was filtered, washed with 400 ml of water and finally subjected to drying at 55-60 C. under vacuum for 4 hours to afford 40 g of title compound having a purity by HPLC of 99.36% and a water content by the Karl Fischer method of 0.27%.

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′-Dicyanobenzophenone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Palle, Venkata Raghavendra Acharyulu; Kalaria, Ashok Jerambhai; Shelke, Sandip Ashok; US2007/100149; (2007); A1;,
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Application of 1835-65-0, 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. 1835-65-0, name is 3,4,5,6-Tetrafluorophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Thetetrafluoro Phthalo nitrile 6.0 g (30mmol), and the potassium fluoride 15 g(1.2eq.) and acetonitrile 20ml were put in the reactor in which the entrance of100ml placing the thermometer was 4 and it was stirred and it cooled to 0. Here, alpha – naphthol 4.3 g(1.0eq.) waslittle by little injected. In 5 orless the mixture after the input end, after it reacted at 1 hour thetemperature was increased to 20 and itreacted 2 hours at 20 through 25. Thereaction mixture was emitted to water after the completion of reaction and the segregatedsolid was filtered and it took out. The obtained crude product was well wipedoff with the methanol and the compound (4-3) 7.2g of the white solid wasobtained (the yield 74percent).

The chemical industry reduces the impact on the environment during synthesis 3,4,5,6-Tetrafluorophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Yamada Kagaku Kogyo Corporation; Yosuke, Manabe; Satoshi, Hayashi; (33 pag.)KR2015/107729; (2015); A;,
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Electric Literature 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.

Step A: 4-bromo-3.5-dimethylbenzamide To a solution of 4-bromo-3, 5- dimethylbenzonitrile (1.0 g, 4.8 mmol) in DMSO (10 ml) at 0 C was added 35% H202 (0.542 mL, 6.19 mmol) and K2C03 (1.32 g, 9.52 mmol). The resulting mixture was stirred at 20 C for2 hours and then poured into water (50 mL). The resulting solid was collected by filtration, then washed with water twice, dried in an oven to give the title compound. ?H NMR (400MHz, CD3OD) oe: 7.62 (s, 2H), 2.46 (s, 6H).

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:
Patent; MERCK SHARP & DOHME CORP.; BIFTU, Tesfaye; BIJU, Purakkattle; COLLETTI, Steven, L.; DANG, Qun; DHONDI, Pawan, K.; GUDE, Candido; JOSIEN, Hubert; KAR, Nam Fung; NAIR, Anilkumar, G.; NARGUND, Ravi, P.; YANG, De-Yi; XIAO, Dong; ZHU, Cheng; WO2015/73342; (2015); A1;,
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These common heterocyclic compound, 1255870-63-3, name is 4-Bromo-2-ethoxybenzonitrile, 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. Formula: C9H8BrNO

A suspension of 4-bromo-2-ethoxybenzonitrile (1.50 g, 6.5 mmol), hydroxylamine hydrochloride (913 mg, 13 mmol) and NaHCOs (1.365 g, 16.3 mmol) in water (1.32 mL) and EtOH (26.6 mL) is stirred in a sealed tube at 90 C for 3h. Once at RT, the product precipitated from the RM upon addition of water. The solid is filtered off under high vacuum, washing with water and some Et20. A first crop of pure title compound (947mg) was thus obtained as white solid. The filtrate is extracted with AcOEt. The organic layer is then washed twice with brine, dried over MgSO4, filtered and concentrated. The residue is purified by FC (hept AcOEt 5:5) to yield another crop of the pure title compound as a white solid (448 mg), merged with the first batch from precipitation. The title compound is obtained as a white solid (1.395 g, 83%). LC-MS A: tR = 0.53min, [M+H]+ = 259.03.

The synthetic route of 4-Bromo-2-ethoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (160 pag.)WO2018/210992; (2018); A1;,
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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. 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2,3,5,6-Tetrachloroterephthalonitrile

0.60g (0.015 mol) of sodium hydroxide was added to a solution of 1.3g(0.0075 mol) of 5-bromopyridin-2-aminein 40 mL of DMF, followed by addition of 2g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring, the mixturewas stirred for 5 hours after addition at room temperature. After the reaction was over by Thin-Layer Chromatographymonitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washedwith water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reducedpressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90°C)= 1:3, as an eluent) to give 2.5 g of compound C-109 as yellow solid, m.p. 154-156°C.[0126] 1H-NMR (300MHz, internal standard TMS, solvent CDCl3) delta(ppm): 9.78(s, 1H, NH), 6.62(d, 1H, Py-3-1H), 7.73(dd, 1H, Py-4-1H), 8.27 (d, 1H, Py-6-1H)

According to the analysis of related databases, 1897-41-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinochem Corporation; Shenyang Research Institute of Chemical Industry Co., Ltd.; LIU, Changling; HUANG, Guang; LAN, Jie; HAO, Shulin; LI, Zhinian; LI, Huichao; GUAN, Aiying; JIANG, Airu; XU, Ying; EP2757092; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 872091-83-3, name is Methyl 4-chloro-3-(cyanomethyl)benzoate, 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 872091-83-3, Application In Synthesis of Methyl 4-chloro-3-(cyanomethyl)benzoate

Add gaseous anhydrous hydrochloric acid for 3 h at 0 C. to a solution of 19.68 g of 4-chloro-3-cyanomethyl-methyl benzoate in 207 ml of methanol.Stir the reaction mixture for 16 h at room temperature, then concentrate at reduced pressure. Take up the residue in 600 ml of ethyl acetate and 500 ml of water. Wash the organic phase with 200 ml of an aqueous solution of sodium chloride, dry over sodium sulphate and concentrate at reduced pressure.The expected product is obtained in the form of crystals.m.p.=55 C.

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, Methyl 4-chloro-3-(cyanomethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2010/69384; (2010); A1;,
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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. 362527-61-5, name is Ethyl 3-bromo-4-cyanobenzoate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 3-bromo-4-cyanobenzoate

STEP 1 : To a pressure vessel were added ethyl 3-bromo-4-cyanobenzoate (500 mg, 1.97 mmol), cesium carbonate (1.28 g, 3.94 mmol), pentan-3 -amine (688 uL, 5.90 mmol), XANTPHOS (1 14 mg, 0.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (90 mg, 0.10 mmol), and dioxane (3 mL). The vessel was sealed and heated to 95 C for 15 h. After cooling to room temperature, the mixture was filtered through celite and the filter cake rinsed with ethyl acetate. The filtrate was then concentrated and the residue was purified by column chromatography (10% ethyl acetate in hexanes) to provide ethyl 4-cyano-3- (pentan-3-ylamino)benzoate (315 mg, 1.21 mmol, 61% yield) as a yellow syrup. 1H NMR (400 MHz, CDCl3): 7.43 (d, IH), 7.33 (s, I H), 7.25 (dd, IH), 4.44-4.35 (m, 3H), 3.48-3.40 (m ,1H), 1..72-1.48 (m ,4H), 1.40 (t, 3H), 0.96 (t, 6H); MS (EI) for Ci5H20N2O2: 261 (MH+).

The synthetic route of 362527-61-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; WO2009/55077; (2009); A1;,
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Electric Literature of 138642-47-4, These common heterocyclic compound, 138642-47-4, name is 2-Bromo-5-methoxybenzonitrile, 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.

General procedure: To a mixture of substituted alcohol 1 (1 mmol) and substituted nitrile 2 (1 mmol), T3P 50 wt% in ethyl acetate (50 mol%) was added and stirred at 90 C. After the reactant disappeared (monitored by TLC), the reaction mixture was cooled to room temperature, excess of water was added and extracted with ethyl acetate and combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by recrystallization using DCM: pet ether (1:9) mixture to get pure compound 3.

The synthetic route of 138642-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chaithra, Nagaraju; Mantelingu, Kempegowda; Rangappa, Kanchugarakoppal S.; Rangappa, Shobith; Sandhya, Nagarakere C.; Swarup, Hassan A.; Synthetic Communications; vol. 49; 16; (2019); p. 2106 – 2116;,
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