Month: September 2021

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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step 1 4-r2-Chloro-4-fluorophenylaminoV5.6.3′.4′.5′.6′-hexahvdro-2’H-?a’1bipyridinyl-2- one [l,r]-Bipiperidinyl-2,4-dione (2.00 g, 10.19 mmol) was dissolved in toluene (8 ml) and 2- chloro-4-fluorophenylamine (1.78 g, 12.23 mmol) was added. More toluene (5 ml) was added. The reaction mixture was boiled under reflux at 110 C for 17 h then allowed to cool. When the reaction mixture reached rt the product precipitated and it was collected by filtration to yield a beige solid (1.80 g, 55%). 1H-NMR (400 MHz, CDCl3) delta 7.41-7.32 (IH, m), 7.18-7.09 (IH, m), 7.00-6.90 (IH, m), 5.51 (IH, s), 5.11 (IH, s), 3.54 (2H, t), 3.38-2.67 (4H, br), 2.57 (2H, t), 1.74-1.50 (4H, m), 1.43-1.30 (2H, m).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/96151; (2008); 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. 69957-83-1, name is N-Ethyl-4-chlorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H12ClN

[4-(2-{[2-(Methoxycarbonyl)phenyl]thio} ethyl) phenoxy] acetic acid (0.200 [G,] 0.577 mmol) was dissolved in DMF (10 ml), [N-(4-CHLOROBENZYL)-N-ETHYLAMINE] (0.108 g, 0.635 mmol) was added and the mixture was cooled to 0 C. N-[(1H-1, 2, 3-benzotriazol-1- yloxy) (dimethylamino) [METHYLENE]-N-METHYLMETHANAMINIUM] tetrafluoroborate (0.204 g, 0.635 mmol) and N-ethyl-N,N-diisopropylamine (0.157 g, 1.212 mmol) were added. The solution was stirred overnight at room temperature. Water (100 [ML)] was added and the water phase was extracted with diethyl ether (3 X 20ml). The organic phase was washed with [NA2CO3] (3 X 20 ml, [AQ)] and HCl (0.5 M, 2 X, 10 [ML).] The organic layer was dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromatography (started with isocratic heptane/EtOAc 30/70 and then the EtOAc concentration was increased to 100%, (silica gel 60 0.004-0. 063 [MM).] The product containing fractions were pooled and the solvent was removed by evaporation to give 0. [085 G OF METHYL 2-{ [2-(4-{2-[(4-CHLOROBENZYL)] (ethyl) [AMINO]-2-] oxoethoxy} phenyl) ethyl] thio} benzoate (yield 29.6%). [1HNMR] (rotamers, 300 MHz, CDC13) : 8 1.09-1. 21 [(M,] 3H), 2.91-2. 99 [(M,] 2H), 3.11-3. 18 [(M,] 2H), 3.32-3. 43 [(M,] 2H), 3.92 (s, [3H),] 4.57-4. 75 [(M,] 4H), 6.78, 6.92 (d, d, 2H), 7.12- 7.46 [(M,] 9H), 7.96 (d, [1H).]

According to the analysis of related databases, 69957-83-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/294; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1127-85-1, name is 2,4-Dichloro-5,6,7,8-tetrahydroquinazoline, 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. Formula: C8H8Cl2N2

2,4-dichloro-5,6,7,8-tetrahydroquinazoline (0.5 g, 2.46 mmol) was added to a round bottom flask and dissolved in tetrahydrofuran (30 mL), and furfurylamine (0.23 mL, 2.46 mmol) and triethylamine (1.03 mL, 7.39 mmol) were added thereto, followed by stirring at 60 C. for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and water was added to the reaction mixture. The resulting mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (ethyl acetate:hexane, 1:1, v/v) to obtain a compound (0.22 g, 34%); 1H NMR (400 MHz, CDCl3) delta 1.82 (s, 4H), 2.28 (s, 2H), 2.68 (s, 2H), 4.68 (d, J=4.8 Hz, 2H), 4.99 (s, 1H), 6.32 (d, J=12.4 Hz, 2H), 7.37 (s, 1H); 13C NMR (400 MHz, CDCl3) delta 21.82, 21.86, 21.91, 31.63, 38.20, 108.01, 110.53, 110.55, 142.37, 151.08, 157.37, 161.42, 164.43.

The synthetic route of 1127-85-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; LEE, So Ha; YOO, Kyung Ho; ROH, Eun Joo; SIM, Tae Bo; KIM, Tae Young; KIM, Jae Ho; (30 pag.)US2019/315726; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 51419-59-1,Some common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, molecular formula is C8H9ClO2S, 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: Sodium hydride (60percent dispersion in mineral oil) (18 mg, 0.45 mmol) was added to a solution of 2-(4-(Piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one (4) (50 mg, 0.15 mmol) in DMF (10 mL), and the mixture was heated at 100 °C. Appropriate sulfonyl chloride (0.22 mmol) in DMF (3 mL) was added slowly to the reaction mixture. The mixture was stirred at 100 °C for 16 h. After cooling, saturated NaHCO3 solution was added. The reaction mixture was extracted with ethyl acetate and the organic phase was washed with brine. The organic phase was dried over MgSO4 and evaporated in vacuo. The residue was washed with ethyl acetate/hexane (1:10) and purified by column chromatography (ethyl acetate) to provide 2-(4-(4-(substituted)-sulfonyl)piperazine-1-carbonyl)phenyl)quinazolin-4(3H)-one.

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rhee, Hee-Kyung; Yoo, Ji Hye; Lee, Eunyoung; Kwon, Young Joo; Seo, Hang-Rhan; Lee, Yun-Sil; Choo, Hea-Young Park; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 3900 – 3908;,
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 7006-52-2 as follows. SDS of cas: 7006-52-2

General procedure: N-Alkyl-substituted aniline (2 mmol) and Ru3(CO)12 in D2O(3mL) (Note: if toluene was needed, 1mL toluene was add as co-solvent) were stirred at 100-140°C in a sealed tube under a N2 atmosphere for 12 h. After the mixture was cooled to room temperature, water (10 ml) was added, and then extracted with diethyl ether (2×10 mL). The organic layer was washed with brine (5 mL), dried over anhydrous Na2SO4,and filtered. The filtrate was concentrated to afford the deuterated aniline product.

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhan, Miao; Jiang, Hongxia; Pang, Xuehai; Zhang, Tao; Xu, Ruixue; Zhao, Lifeng; Liu, Yu; Gong, Yu; Chen, Yuanwei; Tetrahedron Letters; vol. 55; 36; (2014); p. 5070 – 5073;,
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 1005-56-7 as follows. SDS of cas: 1005-56-7

Methyl-5-Jf-acetamido-3 , 5-dideoxy-3- f luoro- 8 , 9- 0-isopropylidene-4- O- (phenoxy) thiocarbonyl-D- eryt+/-ro-/?- L-manno-2 -nonulopyranosonate 19 :19To a solution of 18 (1.949 g, 5.1 mmol) in 70 mL dry DCM and 35 mL pyridine, phenylchlorothionoformate (761 muL, 5.6 mmol) was added at -400C and stirred for 30 minutes at this temperature. The mixture was then brought to room temperature and stirred for further 4 hours. MeOH (5 mL) was then added and after 10 minutes the -crude mixture was concentrated in .vacuo. and purified by column chromatography (EtOAc/MeOH 100:1) to give 19. Colorless solid (2.065 g, 76%) . 1H-NMR (400 MHz, CDCl3) delta 1.35 (s, 3H, Me2C), 1.40 (s, 3H, Me2C), 2.35 (s, 3H, NHAc), 3.49 (m, IH, H-5), 3.86 (s, 3H, OMe), 4.07 (dd, J = 21.5, 10.5 Hz, IH, H-9) , 4.37 (m, IH, H-9′), 4.45 (d, J = 4.9 Hz, IH, H-8), 4.58 (q, J = 2.7 Hz, IH, H-6), 5.16 (dd, J = 25.4, 1.7 Hz, IH, H-3), 5.69 (d, J = 3.6 Hz, IH, H-7), 6.11 (ddd, J = 8.7, 23.1 Hz, IH, H-4) , 6.25 (d, J = 8.2 Hz, IH, NHAc), 7.06 – 7.45 (m, 5H, OPh)

According to the analysis of related databases, 1005-56-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE UNIVERSITY OF BATH; WATTS, Andrew, Graham; WO2010/29302; (2010); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, molecular formula is C6H3BrClN3, 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. 13526-66-4

Example 70(£)-2-(1-(3-((1 -Methyl-1 H-indazol-5-yl)methyl)imidazo[1 ,2-b]pyridazin-6-yl)ethylidene) hydrazinecarboxamide(6-Chloroimidazo[1 ,2-b]pyridazin-3-yl)(1 -methyl-1 H-indazol-5-yl)methanol (70.1)To a solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (232.0 mg, 1.00 mmol) in 5 ml_ THF, was added ethylmagnesium bromide (1.50 ml_, 1.50 mmol) at -10 0C. After stirring at – 10 0C for 1 hour, 1 -methyl-1 H-indazole-5-carbaldehyde (240.0 mg, 1.50 mmol) was added. The mixture was allowed to warm to room temperature slowly and stirred for additional 2 hours. The reaction was quenched with Sat. NH4CI solution and concentrated under reduced pressure. The residue was diluted with water, and extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4 and concentrated. The crude product was washed with DCM to give the title compound as a white solid (230 mg, 70 %). 1H-NMR (400MHz, DMSO-Cf6) delta ppm 8.21 (d, 1 H), 8.02 (s, 1 H), 7.81 (s, 1 H), 7.59 (d, 1 H), 7.56 (s, 1 H), 7.49 (d, 1 H), 7.35 (d, 1 H), 6.29 (d, 1 H), 6.21 (d, 1 H), 4.02 (s, 3H). LCMS (method A): [MH]+ = 314, tR = 4.44 min

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13526-66-4, its application will become more common.

Reference:
Patent; NOVARTIS AG; FU, Xingnian; HE, Feng; LI, Yue; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YU, Zhengtian; ZHANG, Ji Yue (Jeff); DAI, Miao; WO2011/18454; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 14862-52-3, The chemical industry reduces the impact on the environment during synthesis 14862-52-3, name is 3,5-Dibromochlorobenzene, I believe this compound will play a more active role in future production and life.

3,5-dibromochlorobenzene (2.7 g, 10 mmol)9-phenylcarbazole-3-boronic acid (6.0 g, 21 mmol)Sodium carbonate (10.2 g, 96 mmol),Pd2 (dba) 3 (0.4 g, 0.4 mmol), toluene,Ethanol, water 50ml in turn added to the reaction bottle,The reaction was refluxed under nitrogen for 10 hours, cooled to room temperature,The aqueous layer was extracted with ethyl acetate,The organic layers were combined, washed with saturated brine and water, respectively,The organic layer was dried over magnesium sulfate, filtered,Filtrate spin dry, over silicone column,4.4 g of product was obtained, HPLC purity 99.2%.

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, 3,5-Dibromochlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Yu Kaichao; Zhang Zhaochao; Wang Lichun; (35 pag.)CN107056806; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 29671-92-9, name is Carbamimidic chloride 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 29671-92-9, Product Details of 29671-92-9

(1) Add methyl 3-amino-5-bromopyrimidinecarboxylate (6.2 g, 27 mmol) to a 250 mL sealed tube.Chloroformamidine hydrochloride (3.4 g, 30 mmol) and dimethyl sulfone (50.8 g, 20 mmol) were heated to 140oC and stirred for 6 hours. After cooling to room temperature, 50 mL of water was added to the reaction solution, followed by ultrasonication for 30 minutes. The residue was filtered. Water, acetone washing, vacuum drying to obtain a tan solid 1 (yield = 65%),

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, Carbamimidic chloride hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsinghua University; Liao Xuebin; He Lei; Wang Zhisong; Gao Yan; (59 pag.)CN108069963; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics