Category: chlorides-buliding-blocks

Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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. Safety of 2,4,5-Trifluorobenzene-1-sulfonyl chloride

A mixture of 46-1 (1.12g. 10 mmol), 41-1 (2.3g. 10 mmol), pyridine (4g. 50 mmol) and DCM (30 mL) was stirred at room temperature under nitrogen overnight. H20 (30 mL) was added into the mixture which was extracted with DCM. The combined organic layers were washed with brine, dried over Na2504, filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (PE: EtOAc = 5:1) to give 46-2. 1H NMR (400 MHz CD3OD) delta 7.98 (dd, J = 15.6, 8.8 Hz, 1H), 7.75 (dd, J = 16.0, 8.0 Hz, 1H), 7.34~7.41 (m, 1H), 6.90 (t, J = 1.2 Hz, 1H), 6.60 (dd, J = 8, 2 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 220227-21-4, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LI, Dansu; LAYTON, Mark, E.; ROECKER, Anthony, J.; EGBERTSON, Melissa; JONES, Kristen, L. G.; WANG, Xiu; PENG, Xuanjia; WO2015/80988; (2015); A1;,
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Electric Literature of 83121-15-7, 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. 83121-15-7, name is 3,5-Dichloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2.7 mmol of 2,4-difluoro-3,5-dichloro-aniline, and 20 ml of 1,2-dichloroethane in a 100 ml round bottom flask and stirred until the 2,4-difluoro-3,5diclofenac was completely dissolved, was added dropwise with stirring 3 mmol of 4-methyl-1,2,3-thiadiazole-5-formylphenyl isocyanate, dropwise over 15 minutes immediatelythereafter precipitation, followed by stirring at room temperature for 8 hours aftercompletion of the reaction, allowed to stand, the solid product was suction filtered,the filtrate solvent was removed by rotary evaporation, ethyl acetate with a volumeratio of 1:3: recrystallized from petroleum ether after the refrigerator to precipitatea solid, the solid product was combined with 1:3 volume ratio of ethyl acetate:petroleum ether, washed and dried to obtain the product; mp: 187-189 C, yield 92%;

The synthetic route of 3,5-Dichloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lier Chemical co Limited; Nankai University; Fan, ZhiJin; Guo, dandan; fan, Qian; Yang, Wei Qing; Fu, yifeng; Zhao, Hui; Wang, Shouxin; Wang, huan; Mi, Na; (37 pag.)CN102225918; (2016); B;,
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Electric Literature of 6579-54-0, These common heterocyclic compound, 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl 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.

General procedure: Under the condition of ice bath, 4-aminophenol hydrochloride 2 (1.46 g, 10 mmol) was dissolved in pyridine (50 mL). After 2-Naphthalenesulfonyl chloride (2.72 g, 12 mmol) was added drop by drop, the mixture was stirred at room temperature for 5 h (detected by TLC). Solvents were evaporated with the residues being taken up in EtOAc (50 mL). Then the organic layer was washed with saturated 1 N HCl (20 mL * 2), distilled water (20 mL * 2), brine (20 mL * 2), dried over anhydrous MgSO4 and evaporated under vacuum. The residues were purified by EtOH/H2O to give desired intermediate 3a.

The synthetic route of 6579-54-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Fuming; Zhang, Lei; Jia, Yuping; Wang, Xuejian; Li, Xiaoguang; Wen, Qingli; Zhang, Yingjie; Xu, Wenfang; European Journal of Medicinal Chemistry; vol. 69; (2013); p. 191 – 200;,
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Adding a certain compound to certain chemical reactions, such as: 6276-54-6, name is 3-Chloropropan-1-amine hydrochloride, 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 6276-54-6, Quality Control of 3-Chloropropan-1-amine hydrochloride

Step 1: Synthesis of 1-azido-3-aminopropane 1 Synthesis is carried out according to the following reaction scheme: This compound was obtained according to a synthesis previously described by Carboni, B. et al. (Macromolecules, Vol. 40, No. 16, 2007/Carboni, B.; Benanlil, A.: Vaultier, M. J. Org. Chem. 1993, 58, 3736). An aqueous solution (30 mL) of 3-chloropropylamine hydrochloride (4 g; 30.8 mmol) and of sodium nitride (6 g; 92.3 mmol, 3 equiv) is heated at 80 C. for 17 h. After evaporation of the water, the reaction mixture is put in an ice bath. 50 mL of diethyl ether and 4 g of potassium hydroxide are added. The phases are separated. The product is extracted from the aqueous phase with 2*20 ml, of diethyl ether. The organic phase is then dried over magnesium sulfate and filtered. After evaporation, the oil obtained is purified by distillation at reduced pressure. (2.46 g; yield: 80%; colorless oil) 1H NMR (300 MHz, CDCl3), delta (ppm): 3.33 (t, 2H, CH2N3); 2.55 (t, 2H, Cl2NH2); 2.34 (s, 2H, NH2); 1.55 (q, 2H, CH2CH2CH2). FT-IR (ATR, cm-1): 2100 (N3)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Centre National de la Recherche Scientifique; Coudane, Jean; Darcos, Vincent; El Habnouni, Sarah; Garric, Xavier; Lemaire, Laurent; Nottelet, Benjamin; US2014/302324; (2014); A1;,
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Electric Literature of 13078-80-3, 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. 13078-80-3, name is 2-(2-Chlorophenyl)ethanamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Propyl N-cyano-6-amino-3-pyridinecarboximidate (200 mg, 0.98 mmol) and 2-(2-chlorophenyl)ethylamine (170 mg, 1.09 mmol) were dissolved in a mixture of methanol (10 ml) and DMF (1.5 ml), and the mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure and subjected to silica gel column chromatography (Wako Gel C-200, 25 g), and elution was conducted with chloroform:methanol (30:1) to give the title compound (250 mg, yield 85%) as colorless powder. Mp 222 C. IR (KBr) cm-1:3220, 2160, 1570, 740. 1 H-NMR (90 MHz, DMSO): delta (ppm) 8.91(1Hr brs, NH), 8.13(1H, d, J=2.5Hz, H-6), 7.60(1H, dd, J=2.5, 8.6Hz, H-4), 7.45-7.2(4H, C6 H4 Cl), 6.60(2H, brs, NH2), 6.48(1H, d, J=8.6Hz, H-3), 3.56(2H, m, NHCH2 CH2 C6 H4 Cl), 3.02(2H, t, J=7.0Hz, NHCH2 CH2 C6 H4 Cl).

The synthetic route of 2-(2-Chlorophenyl)ethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kirin Beer Kabushiki Kaisha; US5508293; (1996); A;,
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Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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. Product Details of 13726-14-2

Benzoyl isothiocyanate (8.8 mL, 64 mmol) was added dropwise to a solution of 4-chloro- 3-methoxy-benzenamine (10 g, 63 mmol) in 160 mL THF. The mixture was stirred at room temperature for 40 minutes, volatiles were removed and the residue was dissolved in 400 mL methanol. A solution of potassium carbonate (26.3 g, 190 mmol) in 200 mL water was added and the mixture was stirred at room temperature for 90 minutes. The title product (13.5 g, 98%) precipitated after removal of 450 mL of the solvents. MS (m/e): 216.0, 218.0 (M+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13726-14-2, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2005/58887; (2005); A1;,
Chloride – Wikipedia,
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Application of 918538-05-3, 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. 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4a) (0.5 g, 2.7 mmol) in 2-Propanol (6 mL) was added (S)-pyrrolidin-2-ylmethanol (0.39 mL, 4.0 mmol), DIPEA (1.39 mL, 8.0 mmol) and heated at 90 C for 1 hr. The reaction was cooled to room temperature and solid obtained was collected by filtration to afford (S)-(l-(2-chloropyrrolo[2,l-f][l,2,4]triazin-4- yl)pyrrolidin-2-yl)methanol (96a) (0.49 g, 73 % yield) as a white solid; NMR (300 MHz, DMSO-i/e): delta 7.70 (dd, J= 2.6, 1.4 Hz, 1H), 6.97 (dd, J= 4.7, 1.6 Hz, 1H), 6.80 – 6.57 (m, 1H), 5.15 (t, J = 5.7 Hz, 1H, D2O exchangeable), 4.87 (t, J= 5.7 Hz, 1H), 4.44 (d, J= 17.8 Hz, 1H), 4.05 – 3.82 (m, 1H), 3.72 – 3.39 (m, 2H), 2.22 – 1.84 (m, 4H). MS (ES+): 253.3, 255.3 (M+2); MS (ES-): 287.2, 289.2 (M+Cl).

The chemical industry reduces the impact on the environment during synthesis 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; KOTIAN, Pravin, L.; BABU, Yarlagadda, S.; KUMAR, V., Satish; ZHANG, Weihe; LU, Peng-Cheng; RAMAN, Krishnan; (747 pag.)WO2018/232094; (2018); A1;,
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Synthetic Route of 50594-82-6, 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. 50594-82-6, name is 3,4,5-Trichlorobenzotrifluoride, This compound has unique chemical properties. The synthetic route is as follows.

(b) Preparation by a known process, using sodium hydroxide as the base 358 g (1.5 mol) of 3,4,5-trichloro-benzotrifluoride were added dropwise to a mixture of 330 g (3 mol) of resorcinol and 60 g (1.5 mol) of sodium hydroxide in 2 liters of dimethylsulphoxide at 120-130 C. in the course of 7 hours. Thereafter, the reaction mixture was stirred at 130 C. for 8 hours. After cooling to room temperature, the reaction mixture was stirred into a solution of 80 g of sodium hydroxide in 7 liters of water. The insoluble portion was separated off and taken up in toluene; according to the thin layer chromatogram, this solution contained no 2,6 -dichloro-4-trifluoromethyl-3′-hydroxydiphenyl ether. In order to work up the aqueous phase, it was acidified with hydrochloric acid and the oil which separated out was extracted with toluene. After drying, the solvent was stripped off and the residue was distilled. 30 g (6.7% of theory) of 2,6-dichloro-4-trifluoromethyl-3′-hydroxydiphenyl ether were obtained in this manner. Boiling point 123-130 C./0.15 mm Hg.

The chemical industry reduces the impact on the environment during synthesis 3,4,5-Trichlorobenzotrifluoride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Bayer Aktiengesellschaft; US4264769; (1981); A;,
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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 3260-88-6 as follows. Recommanded Product: 3260-88-6

Reference Example 44 2-Chloro-6-methoxybenzyl bromide A mixture of 3-chloro-2-methylanisole (2 g), N-bromosuccinimide (2.39 g) and 2,2′-azobis(2-methylpropionitrile) (32 mg) in carbon tetrachloride (15 mL) was heated at reflux for 3 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane – n-hexane/ethyl acetate = 4/1) to give the title compound (2.9 g).

According to the analysis of related databases, 3260-88-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Chloride – Wikipedia,
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Application of 81927-55-1, 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. 81927-55-1 name is Benzyl 2,2,2-trichloroacetimidate, 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.

To a solution of methyl (3R)-3-hydroxybutanoate (10 g) and benzyl 2,2,2-trichloroethanimidate (23.6 g) in CH2CI2 (300 mL) was added CF3SO3H (7.2 g) and the mixture was stirred at 25C for 12 h. The reaction mixture was concentrated under reduced pressure to remove CH2CI2. The residue was diluted with water (100 mL), extracted with four times with ethyl acetate (90 mL) and concentrated under reduced pressure. The residue was purified by column chromatography (5i02, petroleum ether / ethylacetate, 20:1 to 9:1) to give methyl (3R)-3-benzyloxybutanoate (10 g, 56.7%) as colorless oil. LCMS:209.1 (M÷Hi

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

Reference:
Patent; FLAGSHIP PIONEERING INNOVATIONS V, INC.; CASEY, John P.; BERRY, David; CASTRO, Alfredo; TAYLOR, Steven J.; MASSARI, Ferdinand E.; PROUSFOOT, John; BOGART, Elijah; BRIGGS, Timothy F.; (211 pag.)WO2018/226732; (2018); A1;,
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