Month: September 2021

Related Products 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature 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

Application of 320-51-4, These common heterocyclic compound, 320-51-4, name is 4-Chloro-3-(trifluoromethyl)aniline, 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 S 1-Chloro-4-fluoro-2-(trifluoromethyl)benzene 4-Chloro-3-(trifluoromethyl)benzenamine (19.5 g, 100 mmoles), water (40 ml) and c.hydrochloric acid (40 ml) were heated with stirring on a steam bath until a white solid formed. The mixture was cooled (ice-salt bath) and a solution of sodium nitrite (7 g, 101 mmoles) in water (15 ml) was added over 15 mins. After stirring for a further hour at 0, tetrafluoroboric acid (30 g of 40% aqueous solution) was added dropwise over 15 minutes. After one hour the solid was filtered off, washed with water (10 ml), methanol (30 ml) and ether (30 ml) and then dried in vacuo. The dry compound was heated at 140-180 until no more fumes were observed. The cooled residue was dissolved in ethyl acetate, washed with 5% aqueous sodium hydroxide, dried Na2 SO4) and the solvent was removed in vacuo. The residue was distilled in vacuo (12 mmHg, oven temperature 50-55) to give the sub-title compound as a colourless oil (7.5 g). M+ 200/198; nmr (CDCl3)delta7.8-7.2 (m).

The synthetic route of 320-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fisons plc; US4607041; (1986); A;,
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, Product Details of 72235-58-6

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

Related Products of 445-14-7, 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. 445-14-7, name is 2-Amino-4-chlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 5-chloro-2-(trifluoromethyl)aniline (6.0 g, 30.7 mmol) in acetic acid (16.1 mL, 281 mmol) at rt was added concentrated hydrochloric acid (32 mL, 1053 mmol). To the resulting suspension at 0 °C was added a solution of sodium nitrite (2.54 g, 36.8 mmol) in water (9.2 mL) over 10 min. The mixture was stirred at rt for 4 h before a solution of tin(II) chloride dihydrate (15.23 g, 67.5 mmol) in concentrated hydrochloric acid (32 mL, 1053 mmol) was added over 10 min. The mixture was stirred at rt for 1.5 h. The precipitating solid was collected by suction filtration, then dissolved in water (100 mL), basified with 6N NaOH solution to pH 9, and extracted with EtOAc (4 x 50 mL). The combined extract was dried over MgSO4 and concentrated to a crude solid. The crude was purified with a silica gel flash column, eluting with 0-5percent MeOH in DCM to afford (5-chloro-2-(trifluoromethyl)phenyl)hydrazine (5.35 g, 25.4 mmol, 83 percent yield) as an off- white solid. MS (ESI) m/z: 210.9/212.9 (M+H)+; 1H NMR (400 MHz, METHANOL-d4) delta 7.36-7.44 (m, 2H), 6.79 (br d, J=7.92 Hz, 1H).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-4-chlorobenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JALAGAM, Prasada Rao; NAIR, Satheesh Kesavan; PANDA, Manoranjan; FENG, Jianxin; WANG, Wei; LIU, Chunjian; ELLSWORTH, Bruce A.; SARABU, Ramakanth; SWIDORSKI, Jacob; HARTZ, Richard, A.; XU, Li; YOON, David S.; BENO, Brett R.; REGUEIRO-REN, Alicia; (457 pag.)WO2019/67702; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2533-69-9, A common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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 mixture of 2,3-diaminobenzonitrile (50.0 mg, 376 imol, 1.0 eq) in DCM (1 mL) was added methyl 2,2,2-trichloroethanimidate (86.1 mg, 488 imol, 1.3 eq), followed by the addition of TFA (107.0 mg, 939 imol, 2.5 eq). The mixture was stirred at 18C for 2 hours under N2 atmosphere. The mixture was diluted with 5 mL of DCM and filtered. The filtrate wasused directly into the next step without further purification. The 97.8 mg of cmde 2- (trichloromethyl)-1H-benzo[djimidazole-4-carbonitrile in 5 mL of DCM was obtained as a brown solution and used in the next step directly.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; BURNETT, Duane, A.; VACCA, Joseph, P.; (310 pag.)WO2018/119395; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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

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 933190-51-3 as follows. name: 8-Bromo-6-chloroimidazo[1,2-b]pyridazine

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 104a (2.0 g, 4 mmol), 5-(4-methylpiperazin-1-yl)pyridin-2-amine (920 mg, 4.8 mmol), tris(dibenzylideneacetone)dipalladium(0) (366 mg, 0.4 mmol), XantPhos (688 mg, 1.2 mmol), Cs2CO3 (2.6 g, 8.0 mmol), and 1,4-dioxane (60 mL). After three cycles of vacuum/argon flush, the mixture was heated at reflux for 15 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with dichloromethane/methanol (20:1) to afford 104b as yellow solid (1.4 g, 70%). MS: [M+H]+344.

According to the analysis of related databases, 933190-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; Crawford, James John; Ortwine, Daniel Fred; Young, Wendy B.; US2013/116262; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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

Related Products of 112-26-5, 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. 112-26-5, name is 1,2-Bis(2-chloroethoxy)ethane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a 50 mL round bottom flask imidazole (32 mmol, 2.176 g) and potassium hydroxide (32 mmol, 1.792 g) were dissolved in DMSO (25 mL). The mixture was stirred at 70 for 1 h. After this time, 1,1?-oxybis(2-chloro-ethan (16 mmol, 1.88 ml) was added into the solution and stirred for 24 h under nitrogen atomosphere to complete the reaction which was monitored by TLC. The resulting mixture was poured into 100 mL of water and extracted with methylene chloride (5×20 mL). The combined organic layer was washed with water (3×20mL), dried over Na2SO4 and concentrated to give the crude product, which was further purified by column chromatography over silica gel using CH2Cl2 as eluent to give 1a as a pale yellow viscous oil (2.04 g, Yield = 62% ).

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, 1,2-Bis(2-chloroethoxy)ethane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Ji; Yuan, Yao-Feng; Zhuo, Ji-Bin; Lin, Cai-Xia; Tetrahedron Letters; vol. 59; 11; (2018); p. 1059 – 1064;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics