Tag: M.W=100-200

Synthetic Route of 2401-24-3, 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. 2401-24-3, name is 2-Chloro-5-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product.

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-5-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Chang, Cai-Zhu; Zhu, Hui; Li, Yue-Sheng; Dong, Zhi-Bing; Chemistry Letters; vol. 46; 5; (2017); p. 641 – 643;,
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Synthetic Route of 918538-05-3, These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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: In a 50mL reaction vial, Pd(PPh3)2Cl2 (30mg, 0.042mmol) and NEt3 (121mg, 1.2mmol) were added to a solution of 12 (80mg, 0.424mmol) and 4-trifluoromethoxylphenylboronic acid (90mg, 0.44mmol) in DMF (28.5mL) and H2O (0.5mL). The mixture was stirred at 80C for 4h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, after filtration, the filtrate was evaporated and purified by chromatography (petroleum ether/EtOAc, 20:1) to give the product 13 as a yellow solid (97mg, 78%).

The synthetic route of 918538-05-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xin, Minhang; Zhang, Liandi; Tang, Feng; Tu, Chongxing; Wen, Jun; Zhao, Xinge; Liu, Zhaoyu; Cheng, Lingfei; Shen, Han; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1429 – 1440;,
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Related Products of 367-22-6, A common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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 cooled (-10 C) suspension of 4-chloro-3-fluoroaniline (10.67 g, 73.3 mmol) and Na2CO3 (13.21 g, 125 mmol) in Et20 (300 mL) was added dropwise TFAA (12.23 mL, 88 mmol). The mixture was allowed to warm to rt overnight. The mixture was diluted with hexane (300 mL) and filtered. The filtrate was washed with ice water, 10%aq NaHCO3, and brine, dried over Na2SO4, filtered, and concentrated to give N-(4-chloro-3-fluorophenyl)-2,2,2-trifluoroacetamide (17 g, 96% yield), as a pale, yellow solid. MS(ESI) m/z: 242.1 (M+H).

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CORTE, James R.; DE LUCCA, Indawati; FANG, Tianan; YANG, Wu; WANG, Yufeng; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; EWING, William R.; ZHU, Yeheng; WEXLER, Ruth R.; PINTO, Donald J. P.; ORWAT, Michael J.; SMITH, Leon M. II; WO2015/116886; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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 6775-78-6, COA of Formula: C6H4ClN3

Synthesis of 6-chloro-3-iodoimidazo[l , 2-bJpyridazine To a degassed solution of 6-chloroimidazo[l,2-b]pyridazine (1.0 g, 6.51 mmol) and NIS (2.2 g, 9.77 mmol) in MeCN (30 mL) was heated to 60 C for 10 hours. The reaction mixture was cooled to RT and extract with DCM. The organics were washed with Na2S203 (aq), brine and dried over Na2S04. After concentrated, the crude product was purified by column (PE : EA = 5 : 1) to obtain 6-chloro-3-iodoimidazo[l,2-b]pyridazine (1.4 g, yield: 83%). 1H- MR (CDC13, 400 MHz) delta 7.83 (s, 1H), 7.80 (d, J= 4.8 Hz, 1H), 7.04 (d, J= 9.6 Hz, 1H). MS(M+H)+: 280.

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; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; HABERMANN, Joerg; KOCH, Uwe; NARJES, Frank; LI, Peng; PENG, Xuanjia; SOLL, Richard; WU, Hao; PALANI, Anandan; DAI, Xing; LIU, Hong; HE, Shuwen; DANG, Qung; WO2013/34048; (2013); 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. 67952-93-6, name is 3-Chloro-4-methylbenzylamine, A new synthetic method of this compound is introduced below., Safety of 3-Chloro-4-methylbenzylamine

To a solution of (,S)-3-(5-(aminomethyl)-l-oxoisoindolin-2-yl)azepane- 2,7-dione (TFA salt) (68 mg, 0.176 mmol) in DMF (4 mL) was added CDI (29.0 mg, 0.18 mmol) and the suspension was stirred at RT for 14 h. Then (3-chloro-4-methylphenyl) methanamine (28.0 mg, 0.18 mmol) was added and the mixture was stirred at RT for 8 h. The suspension was diluted with water and extracted with DCM. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the crude product, which was purified by silica gel chromatography eluting with MeOH/DCM from 0% to 10% to give Compound 18 (21.0 mg, 25.1%) as a white solid. MS (ESI) m/z 469 A [M+H] +. MR (400 MHz, DMSO-de) delta 10.69 (s, 1H), 7.66 (d, J=8 Hz , 1H), 7.46 (s, 1H), 7.38 (d, J=8 Hz, 1H), 7.28 (d, J=7.2 Hz, 2H), 7.11 (d, J=8.8 Hz, 1H), 6.64-6.55 (m, 2H), 5.25-5.21 (m, 1H), 4.49 (s, 2H), 4.34 (d, 7 =6 Hz, 2H), 4.19 (d, 7 =6 Hz, 2H), 3.12-3.04 (m, 1H), 2.57 (d, 7 =16.8 Hz, 1H), 2.28-2.23 (m, 1H), 2.29 (s, 3H), 2.12-1.99 (m, 2H), 1.84-1.81 (m, 1H).

The synthetic route of 67952-93-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
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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 15205-15-9 as follows. Computed Properties of C7H7ClFN

Compound 13 was prepared according to the procedure outlined in Scheme 2. The ester was reduced with sodium borohydride (step (a)) and the product alcohol was converted to the corresponding aldehyde utilizing Dess- Martin reagent (step (b)). The aldehyde was condensed with 2-chloro-6- fluorobenzylamine in the presence of anhydrous magnesium sulfate to give an imine, which was subsequently reduced with sodium triacetoxyborohydride to give the secondary amine 13 (step (c)). The imide derivative 16 was also prepared starting with a carboxylic acid which was first converted to the corresponding acid chloride (step (d)). This material was then allowed to react with the anion of 2-chloro-6-fluorobenzamide generated with sodium hydride to give imide 16 in 34% yield (step (e)).

According to the analysis of related databases, 15205-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; THE BRIGHAM AND WOMEN’S HOSPITAL, INC.; TRUSTEES OF BOSTON UNIVERSITY; WO2009/23272; (2009); 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. 53145-38-3, name is 2-Chloro-6-fluoroanisole, A new synthetic method of this compound is introduced below., Computed Properties of C7H6ClFO

2,6-CFA (10.0 g, 62. 28 mmol) was weighed in a separate flask and transferred to a 3-neck, 500-ml round bottom flask equipped with a thermocouple temperature probe, stir bar, and a N2 inlet. The flask was rinsed with anhydrous DME. Additional DME was added to the reaction flask to give a total DME volume of 106 ml. The reaction was cooled to -78C with a dry ice/acetone bath. Once the reaction reached -77C, ft-BuLi (29 ml, 71.62 mmol, 2.5 M in hexanes) was added slowly, dropwise, using a syringe pump over a 45 minute period. The highest temperature reached during addition was -70.1 C. After complete addition of w-BuLi, the reaction was left to stir for 1 hour at -74.1C. After 1 hour, B(OMe)3 (10.5 ml, 93.42 mmol) was added dropwise using a syringe pump over a period of 22 minutes. The highest temperature reached during the B(OMe)3 addition was -67.0C. After the complete addition of B(OMe)3, the dry ice/acetone bath was removed and the reaction mixture warmed to room temperature (about 23.1 C). Once the reaction mixture reached room temperature, the reaction was left to stir an additional 1 hour at that temperature. This procedure was repeated several times to generate a large amount of PBA-diMe in DME. 244.0 g of PBA-diMe in DME (10.3% PBA basis), 27.82 g of 45% KOH, and 108.70 g of deionized water were added to a one liter flask containing a magnetic stirrer. The one liter flask was cooled with a cold water bath to maintain a temperature of 25C to 30C during the additions. The mixture was stirred for about 2 h and was then vacuum filtered to remove lithium salts. Aqueous and organic phases of the mixture were then separated. Concentrated HC1 (40.48 g) was added to the aqueous phase. The aqueous phase was cooled with a cold water bath during the addition of the HC1 to maintain a temperature of 25C to 30C. The aqueous phase was stirred for about 15 minutes to achieve complete dissolution. MIBK (35.91 g) was added to the aqueous phase and the aqueous phase was stirred for about 15 minutes. An organic phase separated from an aqueous phase to give 127.6 g of the organic phase. Analysis of the organic phase gave 17.57% by weight (89.1% yield) of PBA. The organic phase was concentrated to dryness and then placed in a vacuum oven at 50C to give a white solid.

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; DOW AGROSCIENCES LLC; OPPENHEIMER, Jossian; WO2013/101665; (2013); A1;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 39191-07-6, These common heterocyclic compound, 39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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 stirred solution of Step 1 intermediate (100 mg, 0.64 mmol) in THF (6.0 mL) at 0C were added triethylamine (195 mg, 1.93 mmol) and 4-nitrobenzoyl chloride (132 mg, 0.70 mmol). The mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate solution (20 mL)and saturated ammonium chloride solution (20 mL). The organic layer was washed with water (30 mL) and dried over anhydrous sodium sulfate. The residue thus obtained was purified by silica gel column chromatography to yield 152 mg of titled compound. ?H NMR (300 MHz,DMSO-d6): oe 2.82 (s, 3H), 2.94 (s, 2H), 7.38-7.44 (m, 5H), 7.68-7.77 (m, 3H).

The synthetic route of 39191-07-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (98 pag.)WO2017/199103; (2017); A1;,
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Chlorides – an overview | ScienceDirect Topics

Application of 2106-04-9, A common heterocyclic compound, 2106-04-9, name is 3-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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 1: 5-Bromo-N-(3-chloro-2-fluorophenyl)pyridin-3-amineA 20 mL microwave vial was charged with 3-chloro-2-fluoroaniline (473 jiL, 4.22 mmol) and diluted with 1,4-dioxane (16.9 mL). To that solution was added 3,5- dibromopyridine (1000 mg, 4.22 mmol), sodium tert-butoxide (568 mg, 5.91 mmol),xantphos (48.9 mg, 0.0840 mmol), and tris(dibenzylideneacetone)dipalladium(0) (38.7 mg, 0.0420 mmol). The vial was sealed and degassed using ultra pure argon and sonication for 1 mm. The vial was placed into a reaction block preheated to 80 C. After 1 h, the contents of the vial were transferred to a flask, and the volatiles were concentrated under reduced pressure. The resulting brown solids were dissolved with ethyl acetate andwater. The contents of the flask were transferred into a separatory funnel where the layers were separated. The organic was washed with water and brine, dried over magnesium sulfate, and purified by silica gel flash chromatography. Upon dissolving the sample with DCM, a white solid persisted, which was collected by filtration and washed with hexanes to give 541 mg of desired product. The supernatant was concentrated under reducedpressure and purified by silica gel column chromatography (24 g ISCO RediSep Rf, loaded inlwith: DCM and dried, initial waste: 0 mL, fraction size: 9 mL 13x 100 mm, and eluted with ethyl acetate in dichloromethane 0% [75 mL], 0-5% [201 mL], 5% [300 mL]).The fractions were collected and combined with the previously collected solids to give 921 mg(72%). ?H NMR (400MHz, CDC13)oe 8.35 (d,J=2.5 Hz, 1H), 8.31 (d,J1.8 Hz, 1H), 7.58 (t,J=2.1 Hz, 1H), 7.22-7.14 (m, 1H), 7.08-7.01 (m, 2H), 5.86 (br. s., 1H). Mass found 302 [M+H] .

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; DELUCCA, George V.; GAVAI, Ashvinikumar V.; QUESNELLE, Claude A.; GILL, Patrice; O’MALLEY, Daniel; VACCARO, Wayne; LEE, Francis Y.; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; FANG, Haiquan; HILL, Matthew D.; HUANG, Hong; SCHMITZ, William D.; STARRETT, JR, John E.; HAN, Wen-Ching; TOKARSKI, John S.; MANDAL, Sunil Kumar; WO2015/100282; (2015); A1;,
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Related Products of 7149-75-9, 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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Synthesized according to General Procedure 1. 4-chloro-3-methylaniline (5 g, 35.3 mmol) in water (15 mL) and conc. HCl (9.5 mL, 116.5 mmol) at -5¡ã C. was added a freshly prepared aqueous solution of sodium nitrite (3.2 g, 45.9 mmol) in water (8 mL) slowly over 10 minutes. After stirring for 15 minutes at -5¡ã C. a freshly prepared aqueous solution of sodium tetrafluoroborate (5.4 g, 49.4 mmol) in water (14 mL) was added in one portion causing the formation of a precipitate. The solid was filtered and washed with cold (5¡ã C.) diethyl ether (10 mL). The solid was dissolved in acetone (15 mL) and filtered. To the filtrate was added diethyl ether (15 mL) causing the precipitation of the arenediazonium tetrafluoroborate. The solid was filtered, washed with cold (5¡ã C.) diethyl ether (5 mL) and then air dried overnight to provide 4-chloro-3-methylbenzenediazonium tetrafluoroborate (8.07 g, 33.6 mmol, 95percent yield) as a tan solid. 1H-NMR (400 MHz, DMSO-d6) delta 8.68 (d, J=2.2 Hz, 1H), 8.56 (dd, J=2.4, 8.8 Hz, 1H), 8.10 (d, J=8.8 Hz, 1H) and 3.47 (s, 3H) ppm. LC/MS (10percent-99percent CH3CN (0.035percent TFA)/H2O (0.05percent TFA), m/z: M+1 obs=125.0; tR=0.24 min.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; US2010/4300; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics