Month: July 2021

Synthetic Route of 18282-59-2, These common heterocyclic compound, 18282-59-2, name is 4-Bromo-1,2-dichlorobenzene, 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.

Method C; (3,4-Dichloro-phenyl) -(2,2,6,6-tetramethyl-piperidin-4-yl)-amine hydrochloric acid salt; A mixture of 4-amino-2,2,6,6-tetramethylpiperidine (3.4 ml, 20 mmol), potassium tert- butoxide (4.5 g, 40 mmol), 3,4-dichlorobromobenzene (4.97 g, 22 mmol), palladacycle (100 mg, 0.11 mmol) and dioxane (100 ml) was stirred at reflux for 2 h. Water (100 ml) was added and the mixture was extracted with diethyl ether (2 x 50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound. Yield 5.56 g, (82 percent). Hydrochloric acid in ether (6.5 ml, 3.1 M) was added and the hydrochloric acid salt was precipitated and stirred for 10 min, followed by filtration. Mp >300°C.

The synthetic route of 18282-59-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NeuroSearch A/S; WO2005/123679; (2005); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1996-29-8,Some common heterocyclic compound, 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, molecular formula is C6H3BrClF, 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.

1-bromo-4-chloro-2-fluorobenzene (61 g, 291 mmoles), 2,6-dimethoxyphenylboronic acid (50.4 g, 277 mmoles), K2 CO3 (60.4 g, 437 mmoles) and Pd (PPh3) 4 (10.1 g, 8.7 mmoles)Put in a round bottom flask,And then dissolved in 500 ml of THF and 200 ml of distilled water,And the solution was refluxed and stirred at 60 C for 12 hours.When the reaction is complete,The aqueous layer was removed and passed through column chromatography (hexane: DCM 20%)Process the remainder to obtain 38 grams of intermediate 1(51%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-chloro-2-fluorobenzene, its application will become more common.

Reference:
Patent; SAMSUNG SDI CO., LTD.; Kang, Dong Min; Kim, Jun Seok; Lui, Jinhyun; Lee, Byoungkwan; Lee, Sangshin; Won, Jonswoo; Lee, Namheon; Jung, Sung Hyun; Jung, Ho Kuk; (107 pag.)TW2019/43698; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1127-85-1,Some common heterocyclic compound, 1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, molecular formula is C8H8Cl2N2, 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.

This was prepared from MA2-10 (0.114 g) and MA3-034 (0.102 g) using procedure B (reaction time, 4 days). The volatiles were evaporated under the reduced pressure and the product was purified via column chromatography (Si02) eluting with hexanes/EtOAc (1:9 to 1 :2 v/v) to give the title compound MA3-064-1 as a gray solid (0.087 g, 44%). Mp: 265 C (dec). lH NMR (400 MHz, DMSO-ifc): delta 9.67 (s, 1H, disappeared on D20 shake), 8.73 (s, 1H, disappeared on D20 shake), 7.56 (s, 1H), 7.26-7.22 (m, 2H), 7.02-6.98 (m, 1H), 2.62 (t, / = 6.1 Hz, 2H), 2.47-2.43 (m, 2H, partially overlapped by residual DMSO solvent signal), 1.81-1.73 (m, 4H), 1.30 (s, 9H). NMR (400 MHz, CD3OD) delta 7.73-7.70 (m, 1H), 7.27-7.24 (m, 2H), 7.11-7.05 (m, 1H), 4.63 (s, 1H), 2.69 (t, / = 6.0 Hz, 3H), 2.55 (t, / = 6.0 Hz, 2H), 1.92-1.86 (m, 4H), 1.39 (s, 19H). HPLC-MS (ESI+): m/z 397.2 [40%, (M37C1+H)+], 395.2 [100%, (M35C1+H)+]. Procedure B A mixture of substituted 2,4-dichloropyrimidine (1.0 equiv.), and substituted aniline (1.0-1.05 equiv.), and DIPEA (1.2 equiv.) in isopropanol (0.1 M) was stirred and heated at reflux. The reaction time, work-up, and product isolation procedure are described below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, its application will become more common.

Reference:
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; SCHOeNBRUNN, Ernst; LAWRENCE, Nicholas J.; LAWRENCE, Harshani R.; (293 pag.)WO2017/66428; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 870-24-6, 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. 870-24-6, name is 2-Chloroethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-Chloroethanamine hydrochloride (4.6 g, 40 mmol), NEt3 (18 mL, 132 mmol) And 50 mL of methylene chloride. The reaction was stirred at room temperature and trimethylchlorosilane (90 mmol, 9.8 g, 11.4 mL) in dichloromethane (20 mL) was added to the system. The reaction was stirred at room temperature overnight. After the reaction was completed, excess triethylamine, trimethylchlorosilane and methylene chloride were removed under reduced pressure. To the resulting residue was added 60 mL of n-hexane. The reaction was stirred at room temperature for 30 minutes and filtered to remove NEt3.HCl. After the filtrate is concentrated, The target product was obtained by distillation under reduced pressure (6.0 g, 68%).

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-Chloroethanamine hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsinghua University; Liu Qiang; Fu Shaomin; Shao Zhihui; Wang Yujie; (20 pag.)CN107445995; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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;,
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 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,
Chlorides – an overview | ScienceDirect Topics

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

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

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,
Chlorides – an overview | ScienceDirect Topics

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