Author: Jessica.F

These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl chloride, 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. name: Phenylmethanesulfonyl chloride

Preparation 7: N-(2-bromoethyl)(phenyl)methanesulfonamide K2C03 (8.7 g, 62 mmol) was added into a mixture of phenylmethanesulfonyl chloride (6 g, 31 mmol) and 2-bromoethanamine hydrobromide (6.4 g, 31 mmol) in DCM (100 mL) at 0C. And the resulting mixture was stirred at r.t. for 4 hours and left standing overnight. Upon the completion of reaction, water (100 mL) was added in and DCM phase was separated. The aqueous phase was extracted with DCM. The combined organic phase was dried over Na2S04, filetered and concentrated in vacuo to provide a crude which was separated with column chromatography (silica gel with 200 – 300 mesh, 0 to 50% of EtOAc in petroleum ether) to provide compound /V-(2-bromoethyl)(phenyl)methanesulfonamide (7.0 g, 80%) as a pale yellow solid. H NMR (300 MHz, CDC13) delta 7.40 (m, 5H), 4.58 (m, IH), 4.29 (s, 2H), 3.34-3.29 (m, 4H). LCMS (ESI), 300, 302 [M+Na]+, Br pattern found.

The synthetic route of Phenylmethanesulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
Chloride – Wikipedia,
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Related Products of 108-37-2, These common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, 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.

To a solution of diisopropylamine (76 mL, 0.4 mol) in anhydrous THF (664 niL) and n-hexane (220 mL) was added 2.5 M «-BuLi (160 mL, 0.4 mol) dropwise* at -78 0C over 1 h. The mixture was stirred for 1 h at -78 0C and a solution of 1 – bromo-3-chlorobenzene (76 g, 0.4 mol) in anhydrous THF (300 mL) was added dropwise at -78 0C. After stirring for an additional 1 h at the same temperature, a solution of iodine (101 g, 0.4 mol) in anhydrous THF (400 mL) was added dropwise at -78 0C. The temperature was raised from -78 0C to room temperature during 2 h. After stirring for 18 h at rt, the mixture was concentrated in vacuo to give the crude product (120 g) which was distilled under reduced pressure to give l -bromo-3- fluoro-2-iodobenzene (1 15 g, 91%). 1H NMR (400MHz, CDCl3): 7.12-7.18 (t, IH), 7.35-7.41 (dd, IH), 7.49-7.54 (dd, IH); MS (E/Z): 317 (M+H+)

The synthetic route of 108-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; WO2007/117560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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 an oven-dried screw-capped reaction tube equipped with a magnetic stirring bar theketone (1 eq), amine (2.8 eq), 4-nitrophenyl azide (2 eq), acetic acid (10 molpercent) and 4 Amolecular sieves (50 mg) were added. The reaction mixture was dissolved in toluene(0.3M) and stirred at 100 °C for 18 hours. The crude reaction mixture was then directlypurified by column chromatography (silica gel) at first with dichloromethane (DCM) aseluent to remove all 4-nitroaniline formed during the reaction followed by using a mixtureof heptane and ethyl acetate as eluent to afford the corresponding 1,2,3-triazoles asyellow oil.

The synthetic route of 102-49-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karypidou, Konstantina; Ribone, Sergio R.; Quevedo, Mario A.; Persoons, Leentje; Pannecouque, Christophe; Helsen, Christine; Claessens, Frank; Dehaen, Wim; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3472 – 3476;,
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Synthetic Route of 2533-69-9, 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. 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, This compound has unique chemical properties. The synthetic route is as follows.

4-Nitrobenzene-1,2-diamine 1a (19.33g, 126mmol) was suspended in 200mL of glacial acetic acid, methyl 2,2,2-trichloroacetimidate 2a (24.5g, 139mmol) was added dropwise. The mixture was stirred at room temperature until a large amount of solid precipitated. The reaction solution was diluted with 200mL of glacial acetic acid, and then 500g of crushed ice and 100mL of ice water were added, stirred until the ice dissolved. The solution was subjected to suction filtration. The filter cake was washed with water (20mL*5) and subjected to infrared drying to obtain 5-nitro-2-(trichloromethyl)-1H-benzo[d]imidazole 2b (27g, yellow solid), yield: 69%. MS m / z (ESI): 281.8 [M + 1]

The chemical industry reduces the impact on the environment during synthesis Methyl 2,2,2-trichloroacetimidate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Zhejiang Hisun Pharmaceutical Co., Ltd; CHEN, Lei; GUAN, Dongliang; BAI, Hua; YAN, Xing; MIAO, Shuai; ZHU, Songsong; (54 pag.)EP3339305; (2018); A1;,
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Synthetic Route of 6306-61-2,Some common heterocyclic compound, 6306-61-2, name is N-(2-Chloroethyl)propan-2-amine hydrochloride, molecular formula is C5H13Cl2N, 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.

Intermediate 10 (500 mg; 1.26 mmol) then tetrabutylammonium bromide (203.3 mg; 0.63 mmol) were added to a solution of KOH (1.25 g; 18.9 mmol) in 2- methyltetrahydrofuran (15 mL) and water (1 mL) at rt. The reaction mixture was heated at 50C for 1 h, then 2-isopropylaminoethylchloride hydrochloride (CAS 6306- 61-2) (279 mg; 1.77 mmol) was added. The reaction mixture was heated at 50C for 20 hours. The reaction mixture was cooled to rt, then poured into water and brine. EtOAc was added and the organic layer was washed with brine, dried over MgS04, filtered and evaporated to dryness. The residue (0.7 g) was purified by chromatography over silica gel (irregular SiOH, 15-40muetaiota 30g; mobile phase: 0.4% NH4OH, 98% DCM, 2% MeOH). The pure fractions were collected and evaporated to dryness to give 130 mg which was crystallized from Et20 to give 88 mg (14%) of compound 42. MP.: 75C (gum, Kofler).

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

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; BERDINI, Valerio; ANGIBAUD, Patrick Rene; WOODHEAD, Steven John; SAXTY, Gordon; WO2013/61074; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6775-78-6, 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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

6-Chloroimidazo[1,2-b]pyridazine (8.5 g, 0.055 mol) and N-bromosuccinimide (10.0 g, 0.056 mol) were combined in chloroform (250 mL) and refluxed for 4 hours. The reaction was cooled with an ice bath and the solids filtered. The filtrate was diluted with chloroform (150 mL) and saturated Na2CO3 solution (100 mL) and then vigorously stirred for an hour. The organic phase was washed with more saturated Na2CO3 solution and dried over MgSO4. After evaporation, 3-bromo-6-chloro-imidazo[1,2-b]pyridazine was obtained as a tan solid (12.64 g, 98%).MS (ESI (+)m/z): 233.87 (M+H+)1H NMR (CDCl3-d1, 300 MHz), delta 7.83 (d, J=9.3 Hz, 1H), 7.72 (s, 1H), 7.05 (d, J=9.3 Hz, 1H).

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, 6-Chloroimidazo[1,2-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Biogen Idec Ma Inc.; US2011/21513; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 63624-28-2, A common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl chloride, molecular formula is C8H9ClO4S, 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.

A stirred solution of 1- (2′, 4, 4′-trifluoro-1, 1′-BIPHENYL-2-YL) ethylamin (0.71 g, 2.84 MMOL) in DICHLOROMETHANE (5 mL) was treated with 2,4- DIMETHOXYBENZENESULFONYL chloride (0.71 g, 3.0 MMOL), and N, N-diisopropylethylamine (0. 77 g, 6.0 MMOL). The reaction was stirred at room temperature for twelve hours, and the solvent was evaporated in vacuo to a crude oil. The crude oil was purified by preparative liquid chromatography on a BIOTAGE 40 Mi column of pre-packed silica gel (90 g), eluting with a gradient of between 5% and 50% methyl TEFF-BUTYL ether in hexane at a flow rate of 40 mL/min to afford, after evaporation of the solvent, a colorless oil. Crystallization of the colorless oil from ethyl acetate-hexane yielded the title compound (0.93 g, 2.07 mmol, 73%) as a homogeneous, colorless, crystalline solid, m. p. 192- 194C ; MS [ (+ESI), M/Z] : 452 [M+H] + ; MS [(-ESI), M/Z] : 450 [M-H]- ; IR (Solid), A : 3281,1592, 1470,1421, 1319,1136, 1022,817, 681 CM~1 ; 1H NMR (400 MHz, DMSO-d6) 6 : 1.18 (d, J = 6.7 Hz, 3H), 3.79 (s, 6H), 4.05 (m, 1 H), 6.36-6. 56 (m, 2H), 6.98-7. 14 (m, 3H), 7.22 (broad t, 1 H), 7. 26-7.42 (m, 3H), 7.81 (broad d, J = 8.0 Hz, 1 H), exists as approximately 1: 1 mixture of rotamers; Anal. calcd for C22H2OF3NO4S : C, 58.53 ; H, 4.47 ; N, 3.10. Found: C, 58.52 ; H, 4.45 N, 3.13.

The synthetic route of 63624-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WYETH; WO2004/50631; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 626-43-7, 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. 626-43-7, name is 3,5-Dichloroaniline, This compound has unique chemical properties. The synthetic route is as follows.

5.2.1 5,7-Dichloro-2-methylquinoline (B-TDMQ5) To a solution of 3,5-dichloroaniline (3.24 g, 20 mmol) in HCl (12 M, 15 mL) at 0 C acetaldehyde was added dropwise, under stirring. The reaction medium was kept at 0 C for 15 min and the temperature was gradually increased to 80 C. The mixture was stirred at 80 C for 4 h. The resulting mixture was poured into ice-cold water and neutralized with aqueous ammonium. After extraction with CH2Cl2, the organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude mixture was purified by silica gel flash column chromatography (ethyl acetate/petroleum ether, 1/20, v/v). After evaporation of the eluent, B-TDMQ5 was obtained as a yellow solid (2.88 g, 68%). 1H NMR (400 MHz, CDCl3): delta = 8.40 (d, J = 8.0 Hz, 1H), 7.96 (d, J = 2.0 Hz, 1H), 7.55 (d, J =2.0 Hz, 1H), 7.37 (d, J = 8.0 Hz, 1H), 2.76 (s, 3H).

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

Reference:
Article; Zhang, Weixin; Huang, Meijie; Bijani, Christian; Liu, Yan; Robert, Anne; Meunier, Bernard; Comptes Rendus Chimie; vol. 21; 5; (2018); p. 475 – 483;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, belongs to chlorides-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 72235-58-6, HPLC of Formula: C7H7ClFN

Multicomponent reaction First, aldehyde 3 (646.6 mg, 3.6 mmol) and amine 11 (478.8 mg, 3 mmol) were condensed in 3 mL trimethylorthoformiate for 10 hours at room temperature. Then, the solvent was removed in vacuo and the residue was solved in 25 mL o-xylene. Afterwards, succinic anhydride 15 (850 mg, 4.5 mmol) was added and the mixture was heated to 150 C for 24 hours under Dean-Stark conditions. After cooled to room temperature, the solution was concentrated in vacuo. Purification on silica gel (ethyl acetate: methanol = 9:1 -> 1 :1) yielded MCR-product 16 as a diastereoisomeric mixture (33.9 mg, 2.11 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (4-Chloro-3-fluorophenyl)methanamine, and friends who are interested can also refer to it.

Reference:
Patent; PRIAXON AG; BURDACK, Christoph; KALINSKI, Cedric; ROSS, Guenther; WEBER, Lutz; KHAZAK, Vladimir; WO2010/28862; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 873-38-1,Some common heterocyclic compound, 873-38-1, name is 2-Bromo-4-chloroaniline, molecular formula is C6H5BrClN, 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.

To a solution of 2-bromo-4-chloroaniline (15 g) in concentrated hydrochloric acid (85 ml_) is added at -15C a solution of NaNO2 (5.5 g) in water (10 ml_) and the mixture is stirred for 30 minutes. Then the mixture is added at room temperature to a solution of Kl (109 g) in water (200 ml_). After stirring for 18 hours the mixture is partitioned between dichloromethane and 10% aqueous Na2S2O3 solution. The organic phase is washed with 10% aqueous Na2S2O3 solution and brine and concentrated to give the title compund. Yield: 16.4 g; Mass spectrum (El): m/z = 316 [M]+.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; FRATTINI, Sara; HAMPRECHT, Dieter; HIMMELSBACH, Frank; LANGKOPF, Elke; LINGARD, Iain; PETERS, Stefan; WAGNER, Holger; WO2013/144098; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics