Author: Jessica.F

Related Products of 210532-25-5, 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. 210532-25-5 name is 3,5-Difluorobenzene-1-sulfonyl chloride, 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.

1.132 g (5.32 mmol) of 3,5-difluorobenzene-1-sulfonyle chloride is added under argon to a solution of 545 mg (3.55 mmol) of 5-amino-2-chloronicotinotrile in 20 mL of an anhydrous 1:1 mixture of THF and pyridine. The reaction medium is heated to 70C for 3 hours and let 12 additional hours under stirring at room temperature. The solvent is dry evaporated and the crude reaction product is redissolved in ethyl acetate and washed with several aqueous fractions. The organic phase is dried on magnesium sulfate, filtered, concentrated and then purified by silica gel chromatography to yield 784 mg (67%) of N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide. 1H NMR: deltaH ppm (400 MHz, DMSO) : 11,39 (1H, sl, NH), 8. 34 (1H, m, CHarom), 8,10 (1H, m, CHarom), 7,67 (1H, m, CHarom), 7,59 (2H, m, CHarom).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Sokoloff, Pierre; Cachoux, Frederic; EP2689778; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 19393-92-1, 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 19393-92-1 as follows.

EXAMPLE 263 (+-)-{[5-chloro-7-(2,6-dichlorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}amine The title compound was prepared (0.072 g, 8percent) following the general procedure of Example 166 as a white solid, hydrochloride salt from (5-chloro-2-methoxyphenyl)boronic acid (5.0 g, 26.88 mmol) and 2-bromo-1,3-dichlorobenzene (12.14 g, 53.76 mmol). mp 234-236° C.

According to the analysis of related databases, 19393-92-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wyeth; US2005/261347; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 2687-12-9,Some common heterocyclic compound, 2687-12-9, name is Cinnamyl chloride, molecular formula is C9H9Cl, 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: Distilled H2O in a three-necked roundbottom flask ispurged with nitrogen for 30 minutes. PdCl2 and KCl aresubsequently added to the flask and the solution is stirred atroom temperature for 1 h. Then, optionally substituted(R4)-allyl chloride is added and the resulting reactionmixture is stirred at room temperature overnight (18-20 irs).The reaction is extracted with chloroform, and the aqueouslayer washed with chloroform three times. The organiclayers are combined, dried over MgSO4, filtered and concentrated in vacuo. The crude product is recrystallised fromchloroform and methyl tert-butyl ether, and the resultingsolid is isolated by filtration and dried in vacuo; PdCl2 (590 mg, 3.33 mmol); KCl (473 mg, 6.67 mmol); cinnamyl chloride (1.39 mL, 9.99 mmol); H2O (83 mL). Thedimer is obtained as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cinnamyl chloride, its application will become more common.

Reference:
Patent; Johnson Matthey Public Limited Company; Colacot, Thomas; Jon Deangelis, Andrew; (66 pag.)US9777030; (2017); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products 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.

To a solution of compound [1] (1g, 5.31 mmol, 1 eq) in ACN (10 ml) was added successively DIPEA (685 mg, 5.31 mmol, 1 eq) and morpholine (462 mg, 5.31 mmol, 1 eq). The reaction mass was stirred at room temperature for 1 hr. Excess of solvent was evaporated to obtain a yellow solid. Purification of solid residue was done by column chromatography with silica gel (100: 200 mesh) in solvent system 10 % EtOAc in cyclohexane to get compound [2] as an off-white solid (1.1 g, 87%).1H NMR (CDCl3, 300 MHz): d ppm 7.58 (1H,d), 6.74 (1H, dd, J= 4.5,1.2 Hz),6.63 (1H, m), 4.05 (4H, t, J= 4.8Hz), 3.85 (4H, t, J= 4.8 Hz); ESIMS: 238 (M+ + 1).

Statistics shows that 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine is playing an increasingly important role. we look forward to future research findings about 918538-05-3.

Reference:
Article; Dugar, Sundeep; Hollinger, Frank P.; Kuila, Bilash; Arora, Reena; Sen, Somdutta; Mahajan, Dinesh; Bioorganic and Medicinal Chemistry Letters; vol. 25; 16; (2015); p. 3142 – 3146;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 6306-61-2, name is N-(2-Chloroethyl)propan-2-amine hydrochloride, 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. Formula: C5H13Cl2N

In anhydrous conditions under argon atmosphere, NaH (60% in mineral oil, 0.232 g, 5.8 mmol) was added slowly to a suspension of intermediate 9 (0.35 g, 0.97 mmol) in N,N- dimethylformamide (10 ml) at 0C and the mixture was stirred at 0C for 10 minutes. Isopropylaminoethyl chloride hydrochloride (0.459 g, 2.9 mmol) was added portionwise and the reaction mixture was stirred at room temperature for 48 h ours. The reaction mixture was quenched with a saturated solution of ammonium chloride (15 ml) and the mixture was extracted with ethyl acetate (3 x 50 ml). The combined organic layers were washed with a saturated solution of sodium chloride (2 x 50 ml), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified bychromatography over silica gel (mobile phase, gradient from 95% DCM, 5%MeOH to 90% DCM, 10%). The fractions were collected and the solvent was evaporated yielding 0.22g of fraction 2 composed of a mixture of compound 4 and compound 6..Fraction 1 and Fraction 2 were combined and purified by achiral SFC (mobile phase, 0.3% isopropylamine, 86% C02, 14% MeOH). The desired fractions were collected and concentrated, yielding 17 mg of compound 5, 168 mg of compound 4 and 60 mg of product fraction 3 containing compound 4 and compound 6..Compound 4 was converted into the HCI salt (3eq. 1 M solution in water) in Et20 and triturated . The precipitate was filtered off, washed with Et20 and dried under vacuum, yielding 153 mg of compound 4 (mp = 175C Kofler).Product fraction 3 was purified by chiral SFC on (5muiotaeta mobile phase, 0.3%isopropylamine, 85% C02, 15% MeOH), yielding 22mg of compound 6.

The synthetic route of N-(2-Chloroethyl)propan-2-amine hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; ANGIBAUD, Patrick Rene; OBRINGER, Michel; MARIN, Julien Jeremie Joseph; JEANTY, Matthieu; WO2013/61077; (2013); 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. 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 39065-95-7

To a solution of (R)-7-bromo-2-(difluoromethyl)-1-(1-hydroxypropan-2-yl)-1H-benzo[d]imidazole-5-carboxylic acid (5c, 100 mg, 0.286 mmol, 1 eq) and 4-(chlorodifluoromethoxy)aniline (1h, 66.54 mg, 0.344 mmol, 1.2 eq) in DMF (2 mL) was added HATU (130.69 mg, 0.344 mmol, 1.2 eq) and DIEA (148.08 mg, 1.15 mmol, 199.56 uL, 4 eq). The mixture was stirred at 15 C. for 12 hr. LCMS showed 5c was consumed completely and desired MS was detected. The mixture was diluted with water (5 mL) and extracted with EtOAc (10 mL*3). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give the crude residue. The residue was purified by prep-TLC (SiO2, ethyl acetate_methanol=10:1) to afford 5e as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 10.56 (s, 1H), 8.49 (s, 1H), 8.21 (s, 1H), 7.93 (d, J=9.3 Hz, 2H), 7.43-7.71 (m, 1H), 7.38 (br d, J=9.0 Hz, 2H), 6.02 (br d, J=6.2 Hz, 1H), 5.23-5.45 (m, 1H), 3.72-3.93 (m, 2H), 1.60 (br d, J=6.8 Hz, 3H).

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 39065-95-7.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2, A common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Preparation 32 1-Bromo-3-chloro-5-methoxybenzene Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2*20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluding with cyclohexane to provide the title compound (302 mg) as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.77 (s, 3H), 6.82 (s, 1H), 6.94 (s, 1H), 7.09 (s, 1H). Microanalysis: Found: C, 37.94; H, 2.75. C7H6BrClO requires C, 37.96; H, 2.73%.

The synthetic route of 33863-76-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, 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. COA of Formula: C5H10ClO3P

In a reflux condenser, thermometer, stirrer,Constant pressure dropping funnel 2000mL four-necked flask was added 74g of cyclic phosphorus oxychloride,8 g of anhydrous aluminum trichloride and 800 mL of toluene were added to dissolve them with stirring.Under stirring at 10 C,22.8gBetween cyclohexane diamine four-necked flask,After the addition of cyclohexane diamine is completed,The temperature was raised to 80 C,And the reaction at this temperature 6h, after the reaction was recovered by vacuum distillation solvent,The residue was washed three times with deionized water to give a white solid powder,After drying at 60 C for 10 h, 73.3 g of a product was obtained in a yield of 89.8% by weight.

The synthetic route of 4090-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sinopec Corporation; Sinopec Corporation Fushun Petrochemical Institute; Zhao Wei; Wang Xiaolin; Li Ming; Liu Mingrui; Xue Qian; (8 pag.)CN104558039; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 29882-07-3, These common heterocyclic compound, 29882-07-3, name is 4-Chloro-1,1-dimethoxybutane, 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.

2. 2-(5-Cyanomethyl-1H-indol-3-yl)ethylamine. Hydrochloride 4-Chlorobutanal dimethylacetal (37.07 g, 0.24 mol) was added to a stirred solution of 4-hydrazinobenzyl cyanide hydrochloride (47.0 g, 0.26 mol) in EtOH/H2 O (5:1; 21) and refluxed for 4.5 h. The reaction mixture was evaporated to dryness under vacuum, MeOH (150 ml) added, and the mixture left at 0° C. for 10 h. The resultant pale yellow precipitate was filtered under vacuum, washed with Et2 O/MeOH (5:1; 2*100 ml) and dried. The product was used without further purification (24.1 g, 40percent), m.p. 239°-241° C.; Rf 0.4 in CH2 Cl2 /EtOH/NH3 (40:8:1); 1 H NMR (360 MHz, D2 O) 3.18 (2H, t, J=7.1 Hz, CH2); 3.36 (2H, t, J=7.1 Hz, CH2); 4.02 (2H, s, CH2); 7.22 (1H, dd, J=1.5and 8.4 Hz, Ar-H); 7.36 (1H, s, Ar-H); 7.56 (1H, d, J=8.4 Hz, Ar-H); 7.66 (1H, s, Ar-H).

Statistics shows that 4-Chloro-1,1-dimethoxybutane is playing an increasingly important role. we look forward to future research findings about 29882-07-3.

Reference:
Patent; Merck Sharp & Dohme Limited; US5298520; (1994); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2533-69-9,Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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 3-bromo-4-chlorobenzene-1,2-diamine (4 g, 18 mmol) in AcOH ( 30 mL) was added methyl 2,2,2-trichloroacetimidate (3.5 g, 20 mmol) drop wise at 0 C. Then the reaction mixture was stirred at room temperature overnight. The mixture was poured into water (200 mL), and precipitate was collected and dried to give 4-bromo-5-chloro-2-(trichloromethyl)-1H-benzo[djimidazole (5.5 g, 80%) as a white solid. HPLC/UV purity: 95%; LC-MS (ESI): 349.1 (M + 1).

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

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; PINKERTON, Anthony B.; ARDECKY, Robert J.; ZOU, Jiwen; (256 pag.)WO2018/204176; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics