Category: chlorides-buliding-blocks

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;,
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. 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2770-11-8, 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. 2770-11-8 name is 2-(4-Chlorophenoxy)aniline, 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.

4-[2-(4-Chlorophenoxy)phenylcarbamoyI]piperidine-l-carboxylic acid fer/-butyl ester (AMR01031) C23H27ClN2O4, MW 430,92A solution of piperidine-l,4-dicarboxylic acid mono-tert-butyl ester (AMRO 1030, 417 mg, 1.82 mmol) in dry DCM (8 mL) was stirred under nitrogen, and 4- dimethylaminopyridine (DMPA, 40 mg, 0.327 mmol), (l-(3-dimemylaminopropyl)-3- ethylcarbodiimide hydrochloride (EDC, 1.05 g, 5.46 mmol) and triethylamine (0.25 mL) were added. The resulting mixture was stirred for 30 min under nitrogen and 2-(4-chloro- phenoxy)-phenylamine (AMR01029, 400 mg, 1.82 mmol) in dry DCM (4 mL) was added. After stirring at room temperature for 24 h, the mixture was diluted with DCM, washed EPO with HCl IM (3 x 25 mL), water, saturated NaHCO3 (2 x 25 mL) and brine. The organic layer was dried (MgSO4), filtered and evaporated. Flash chromatography on silica gel of the crude product using hexane/EtOAc 8:2 as eluent gave starting material (104 mg). Further elution using hexane/EtOAc 7:3 gave 4-[2-(4-chlorophenoxy)- phenylcarbamoyl]piperidine-l-carboxylic acid tert-butyl ester (430 mg, 55%) as a white solid, mp 97-99 0C. Rf: 0.22 (hexane/EtOAc 7:3) LC/MS (APCI) tr = 3.83 min, m/z 431.23 (33), 429.21 (M’-H,100). 1H NMR (270 MHz, CDCl3) ¡ê 1.44 (9H5 s, 3CH3), 1.68 (2H, m, CH2), 1.83 (2H, m, CH2), 2.36 (IH, tt, J= 11.4, 3.7 Hz), 2.75 (4 H, br t, 2CH2), 4.11 (4H, m, 2CH2), 6.81 (IH, dd, J= 8.2, 1.5 Hz, ArH), 6.93 (2H, AA’BB’, ArH), 7.01 (IH, td, ArH), 7.12 (IH, td, ArH), 7.31 (2H, AA’BB’, ArH), 7.68 (IH, br s, NH) and 8.40 (IH, dd, J= 6.9, 1.5 Hz, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Chlorophenoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; STERIX LIMITED; WO2007/3934; (2007); A2;,
Chloride – Wikipedia,
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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13918-92-8, 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 13918-92-8 as follows.

General procedure: To a solution of 5-bromo-2-methoxypyridin-3-amine (1) (2.01 g,10 mmol) in pyridine (50 ml) at 0 C, 4-fluorophenylsulfonylchloride (2.14 g, 11 mmol) was added. Then the mixture was stirredat room temperature for 24 h. Pyridine was removed underreduced pressure and adding water (100 ml), extracted with ethylacetate (3 100 ml), the organic layer was washed with water(50 ml), dried with Na2SO4 and evaporated to give compound 2a asa white solid (3.22 g, 89.4% yield).

According to the analysis of related databases, 13918-92-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fan, Yan-Hua; Li, Wei; Liu, Dan-Dan; Bai, Meng-Xuan; Song, Hong-Rui; Xu, Yong-Nan; Lee, SangKook; Zhou, Zhi-Peng; Wang, Jian; Ding, Huai-Wei; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 95 – 106;,
Chloride – Wikipedia,
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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 174913-12-3, A common heterocyclic compound, 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, molecular formula is C7H6BrClO, 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.

Bromo-3-chloro-5-methoxybenzene (10 mmol, 2.2 g)Diphenylamine (20 mmol, 3.34 g) was added to a 100 mL three-necked flask,A cuprous iodide (2 mmol, 0.4 g) was added under nitrogen,Potassium carbonate (20 mmol, 1.4 g),O-phenanthroline (2 mmol, 0.4 g),50 mL of DMF,Reaction was carried out at 155 C for 3 days;The resulting reaction product is subjected to extraction,The extracted organic phase was evaporated to dryness with ethanol,Then recrystallized from ethyl acetate and petroleum ether,To obtain 1.83 g of intermediate A-1,

The synthetic route of 174913-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jilin Aolai De Optoelectronic Materials Co., Ltd.; Gao, Chunji; Cui, Dunzhu; Sun, Yi; Zhang, Chengcheng; (52 pag.)CN104892434; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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

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. 22680-44-0, name is (2-Chlorophenyl)methanamine hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

45-1) 5-Hydroxymethyl-1-(2-chlorobenzyl)imidazole The title compound was obtained in a yield of 60% according to the same procedure as Preparation 31-1) using dihydroxyacetone and 2-chlorobenzylamine hydrochloride as sting materials. 1H NMR(CDCl3) delta3.24(s, 2H), 4.44(s, 2H), 5.26(s, 2H), 6.78(d, 1H), 6.90(s, 1H), 7.15(m, 1H), 7.21(m, 1H), 7.34(d, 1H), 7.38(s, 1H)

According to the analysis of related databases, 22680-44-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LG Chemical Ltd.; US6268363; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13726-14-2, name is 4-Chloro-3-methoxyaniline, 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 13726-14-2, Recommanded Product: 4-Chloro-3-methoxyaniline

5-NITRO-2-CHLORO aniline (50.0 g, 0.289 mol) in 30 % sulfuric acid (300 ml) was stirred at RT FOR 2 h. Sodium nitrite (21.0 g, 0.304 mol) in water (50 ml) was added slowly at 0C and maintained at this temperature for 15 min. This diazotized solution was added slowly to dilute sulfuric acid (50 %, 250 ML) at 110 C. Stirring was continued for 15 min. After cooling to RT, ice water was added, the mixture extracted with ethylacetate, washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield 12.0 g, 24. 0 %. [00162] To K2CO3 (23.84 g, 0.172 mol) and 2-chloro-5-nitrophenol (10.0 g, 0.0576 mol) in ACETONITRILE (100 ml) was added methyl iodide (19.60 g, 0.138 mol) at 0C. The reaction mixture was warmed to RT and stirred overnight. Water was added and extracted with ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield : 6.0 g, 55. 55 %. [00163] 2-CHLORO-5-NITRO ANISOLE (6.0 g, 0.032 mol) in MEOH (45 ml) was added slowly to stannous chloride (15.1 g, 0.08 mol) in conc. HCI (110 ml) at 40 C and the temperature was slowly raised to 50 C. Stirring was continued for 2h, the reaction cooled to RT, basified with 50 % NAOH solution and extracted by ethyl acetate. The organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield : 4.0 g, 79.36 %. [00164] To triethylamine (3.83 g, 0.037 mol) and 3-methoxy-4- chloro aniline (3.0 g, 0.0190 mol) in benzene (50 ML) was added trimethylacetylchloride (2.75 g, 0.022 mol) slowly at 0 C. The temperature was raised to RT and stirred overnight. The reaction mixture was added to ice and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over NA2SO4 and concentrated. Yield : 3.7 g, 80.43 %. [00165] To N-PIVALOYL-3-METHOXY-4-CHLOROANILINE (1.50 g, 0.0062 mol) in THF (30 ML) was added n-butyl lithium (1.0 g, 0.0156 mol) at 0 C and the reaction stirred for 2 hr. After cooling to-70 C, methyl isonicotinate (1.3 g, 0.0094 mol) in THF (12 ml) was added slowly. The reaction was warmed to rt and stirred overnight and then quenched with water and extracted with ether. The water layer was further extracted and the combined ether layers were washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography. Yield 0.50 g, 23. 25 %. [00166] The protected ketone from step 5 (0.500g, 0. 0014MOL) was suspended in concentrated HCI (5 ml) at RT, then the temperature was raised to 95 C and the mixture stirred over night. The mixture was cooled to RT, basified with 20 % NAOH solution and extracted with DCM. The combined organic layer was washed with water, brine and dried over NA2SO4. The product obtained upon concentration was purified by column chromatography using basic alumina to yield title compound (0.140 g, 37.33%).

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-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHEMOCENTRYX; WO2004/46092; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics