Month: March 2021

Reference of 59681-66-2, These common heterocyclic compound, 59681-66-2, name is 4-Chloro-N1-methylbenzene-1,2-diamine, 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.

EXAMPLE 35 Preparation of 7-Chloro-4,9-dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one A 532 mg. portion of 7-chloro-1,3,4,9-tetrahydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one (prepared by the reaction of 4-chloro-2-amino-N-methylaniline and 3-keto-4 -carbomethoxy tetrahydro thiophene at relfux temperature in tolune) is suspended in 4 ml. of pyridine. A 276 mg. portion of N-chlorosuccinimide is added in portions while rinsing with 1 ml. of pyridine. The mixture is heated on a steam bath for 15-20 minutes, cooled and diluted with water yielding a brown solid which is recrystallized twice from methanol yielding 0.25 g., m.p. 244-246C.

The synthetic route of 59681-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US3953430; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, A new synthetic method of this compound is introduced below., Quality Control of 3-Chloro-2-fluoroaniline

3.25 ml phosphorus oxychloride are added dropwise to 6.50 g 6-(1,4-dioxa-spiro[4.5]dec-8-yloxy)-7-methoxy-3H-quinazolin-4-one in 65 ml acetonitrile under an argon atmosphere. Then the reaction mixture is heated to 40 C., combined dropwise with 5.00 ml triethylamine and refluxed for 2 h. After cooling to ambient temperature 1.40 ml triethylamine and 2.60 ml 3-chloro-2-fluoro-aniline, dissolved in 5 ml acetonitrile, are added and the reaction mixture is stirred overnight at 40 C. Then a further 0.70 ml of 3-chloro-2-fluoro-aniline dissolved in 2 ml acetonitrile are added dropwise and the reaction mixture is stirred for a further 10 h. After cooling to ambient temperature the precipitate formed is suction filtered, taken up in 1 N hydrochloric acid, combined with 6 N isopropanolic hydrochloric acid and stirred at ambient temperature until the ketal cleaving is complete. The precipitate formed is suction filtered and combined with methylene chloride and 1 N sodium hydroxide solution. The aqueous phase is separated off and extracted with methylene chloride, the combined extracts are evaporated down and the flask residue is brought to crystallisation with diisopropylether.Yield: 5.90 g (73% of theory)Mass spectrum (ESI+): m/z=416, 418 [M+H]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/46148; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 4584-46-7, The chemical industry reduces the impact on the environment during synthesis 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, I believe this compound will play a more active role in future production and life.

A solution of 5-nitroindoline (6) (0.5 g, 3.05 mmol) in DMF (10 mL) was treated with NaH (0.39 g, 9.75 mmol, 60% wt in mineral oil) at 0 C resulting in an orange mixture. ;The reaction mixture was then treated with 2-chloro-N,N-dimethylethanamine hydrochloride (0.87 g, 6.09 mmol) resulting in a dark red mixture. ;The reaction was heated to 90 C and stirred for 1.5 h. ;After allowing the reaction to cool to room temperature, water was added and the product was extracted into EtOAc. ;The combined ethyl acetate layer was washed with water, brine and dried (Na2SO4). ;Solvent was evaporated and the crude was purified by flash column chromatography (2 M NH3 in MeOH:CH2Cl2, 2.5:97.5) to obtain the title compound (0.4 g, 56%) as a solid. 1H NMR (DMSO-d6) delta 7.96 (dd, 1H, J = 2.1, 8.7 Hz), 7.79 (d, 1H, J = 2.1 Hz), 6.49 (d, 1H, J = 9.0 Hz), 3.72 (t, 2H, J = 8.7 Hz), 3.39 (t, 2H, J = 6.6 Hz), 3.04 (t, 2H, J = 8.7 Hz), 2.44 (t, 2H, J = 6.3 Hz), 2.18 (s, 6H).

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-Chloro-N,N-dimethylethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 626-43-7, These common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, 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.

EXAMPLE 5; Preparation of 1,3,5-triaminobenzene from 3,5-dichloroaniline, hydrolysis with hydrochloric acid of the 1,3,5-triaminobenzene to phloroglucinol; A pressurized vessel is charged with 30 g (18.6 mmol) of 3.5-dichloroaniline and 1.8 g of copper iodide in 160 ml of 28% aqueous ammonia. The mixture is heated at 190 C. and under a pressure of 40 bars for 24 h. The contents of the vessel are poured into 200 ml of water and then the excess ammonia is removed. Then 56 g of 10 N hydrochloric acid are added and the mixture is heated at 110 C. for 20 h. Following filtration, the solution is cooled in an ice bath until the phloroglucinol precipitates. The precipitate obtained is subsequently recrystallized from 400 ml of a water-methanol (95 V-5 V) mixture.

Statistics shows that 3,5-Dichloroaniline is playing an increasingly important role. we look forward to future research findings about 626-43-7.

Reference:
Patent; PHV ANALYITIC; US2005/165256; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-41-8,Some common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, molecular formula is C7H7Cl, 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: Under N2 atmosphere, KOtBu (1.3 equiv), toluene (1.0 mL), amines 5 (0.84 mmol), aryl chlorides 4 (0.7 mmol) and finally a solution of complex 3a (20-100muL, 0.01-0.05 mol%, prepared from 0.014 mmol 3a in 4.0mL toluene) were successively added into a Schlenk reaction tube. The mixture was stirred vigorously at 110 C for 24h. Then the solvent was removed under reduced pressure and the residue was purified by flash column chromatography (SiO2) to give the corresponding products.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloro-3-methylbenzene, its application will become more common.

Reference:
Article; Liu, Feng; Hu, Yuan-Yuan; Li, Di; Zhou, Quan; Lu, Jian-Mei; Tetrahedron; vol. 74; 39; (2018); p. 5683 – 5690;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 821-10-3,Some common heterocyclic compound, 821-10-3, name is 1,4-Dichlorobut-2-yne, molecular formula is C4H4Cl2, 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: K2CO3 (3a, 210 mg, 1.5 mmol) was added to a solution of b-ketoesters 5a-c (0.5 mmol) in acetone (10 mL) at 25 C. The reaction mixture was stirred at 25 C for 10 min. 1,4-Dichloro-2-butyne (2, 68 mg, 0.55 mmol) was added to the reaction mixture at reflux. The reaction mixture was stirred at 56 C for 8 h. The reaction mixture was cooled to 25 C and the solvent was concentrated. The residue was diluted with water (10 mL) and the mixture was extracted with CH2Cl2 (320 mL). The combined organic layers were washed with brine, dried, filtered and evaporated to afford crude product. Purification on silica gel (hexanes/EtOAc20/1e10/1) afforded 6a-c.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,4-Dichlorobut-2-yne, its application will become more common.

Reference:
Article; Chan, Chieh-Kai; Lu, Yi-Ju; Chang, Meng-Yang; Tetrahedron; vol. 71; 51; (2015); p. 9544 – 9549;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2729-34-2, 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. 2729-34-2 name is 3,5-Dichloro-4-fluoroaniline, 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.

To a suspension of ethyl 2-cyanoacetimidate hydrochloride (0.50 g, 3.36 mmol, Eq: 1.00) in ethanol (5.2 mL), was added 3,5-dichloro-4-fluoroaniline (606 mg, 3.36 mmol, Eq: 1.00). The suspension was stirred overnight at room temperature, under a nitrogen atmosphere. The reaction mixture was filtered to remove the salts. The clear yellow filtrate was then treated with hydrazine (in water) (313 mg, 310 mu, 3.42 mmol, Eq: 1.02) and heated in an oil bath at 80- 85C for 4.5 h. The reaction was cooled to room temperature and concentrated. The residue was partitioned between EtOAc and water. The organic phase was removed, washed with brine, dried (Na2S04) and concentrated over celite. The crude material was purified by flash chromatography (silica gel, SF 15-24 g, 20% to 100% EtOAc in hexanes) to give a light brown oil, which was further purified by HPLC (reverse phase, Sunfire Prep C18 OBD [5 uM; 30×100 mm], 5% to 95% acetonitrile in water (each containing 0.1% TFA)). The product-containing fractions were combined and freeze-dried. The freeze-dried material was taken up in EtOAc and washed with aqueous NaHC03 (lx) and water (2x). The organic phases was dried (Na2S04) and concentrated. The residue was dissolved in acetonitrile-water and freeze-dried to give 45 mg (5%) of desired product as an off-white solid. MS m/z 261, 263 [M+H]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichloro-4-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Chloro-3,5-dimethoxybenzene

1-Chloro-3,5-dimethoxybenzene (70g, 406mmol) and Pyridine Hydrochloride (468g, 4055mmol) are placed in a round bottom flask and refluxed at 200 C for 24 hours. After the reaction is completed, cool to room temperature and slowly pour into distilled water and stirred for 1 hour.The solid was filtered to give 51.6 g (88%) of intermediate (Int-7).

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 7051-16-3.

Reference:
Patent; Samsung SDI Co., Ltd; Samsung Electronics Co., Ltd.; Lee Seung-jae; Kim Chang-u; Kim Byeong-gu; Kim Hyeong-seon; Ryu Dong-wan; Shin Chang-ju; Jang Gi-po; Seo Min-seok; Jeong Seong-hyeon; (39 pag.)KR102044943; (2019); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2589-11-9, name is 6-Chloro-1H-imidazo[4,5-c]pyridine, belongs to chlorides-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 6-Chloro-1H-imidazo[4,5-c]pyridine

C2. Methyl 5-(6-chloro-1H-imidazo[4,5-c]pyridin-1-yl)-3-hydroxythiophene-2-carboxylate (Compound C2a) and Methyl 5-(6-chloro-3H-imidazo[4,5-c]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate (compound C2b) To a mixture of 0.68 g of 6-chloro-1H-imidazo[4,5-c]pyridine and 0.65 g of 2,2,6,6-tetramethylpiperidine in 100 ml chloroform is slowly added a solution of 0.87 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 40 ml chloroform. The reaction mixture is stirred for 12 h at room temperature. After washing with water (3 x 50 ml) the organic layer is separated, dried with MgSO4 and concentrated to a volume of about 100 ml. The residue is treated with n-hexane until precipitation takes place. The solid is filtered and the procedure is repeated once again. The combined solids are dried under vacuum to yield the title compounds as an isomeric mixture, which is used for the next step (example B3) without further purification. LC-MS (MH+ found) = 310.0 (isomeric mixture)

The synthetic route of 2589-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, 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. category: chlorides-buliding-blocks

Example 3 General Procedure C To the aryl halide (2.0 mmol), Pd2(dba)3 (37 mg, 0.04 mmol, 2 mol %) and 2-(dicyclohexylphosphino)biphenyl (34 mg, 0.1 mmol, 4.8 mol %) were added LiHMDS (803 mg, 4.8 mmol, 2.4 equiv.) and 4 mL toluene. The reaction mixture was stirred at room temperature for 17 h. At reaction completion, the mixture was quenched with 1N HCl (5 mL) and stirred at room temperature for 5 min. Then, it was basified to pH=12 with 1N NaOH and the layers were separated. The organic layer was concentrated. 5-Chlorobenzene-1,3-diamine General Procedure C was followed using 5-chloro-1,3-dibromobenzene (540 mg, 2.0 mmol). The product was isolated as a brown oil in 97% yield (299 mg, 105% mass recovery and 83% purity). 1H NMR (400 MHz, CDCl3): delta 6.10 (s, 2 H), 5.87 (s, 1 H), 3.60 (br s, 4 H); 13C NMR (100 MHz, CDCl3): delta 148.3, 135.5, 105.9, 99.7; HRMS calcd for C6H8N2Cl (M+H) 143.0370, found 143.0369.

The synthetic route of 3,5-Dibromochlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International, GmbH; US2006/258888; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics