Tag: M.W=100-200

4863-91-6, 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 4863-91-6 as follows.

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
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433-94-3, 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. 433-94-3, name is 2-Chloro-6-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A) 15 g of hydrochloric acid (0.15 mol) are added to the reaction apparatus,After cooling, 9.2 g (0.047 mol) of 2-chloro-6-trifluoromethylaniline was dropwise added to the system,Dropping added insulation reaction 60min,Then sodium nitrite solution 13.5g (0.09mol) was added dropwise to the system,Process temperature 3 ,Dropping added insulation reaction 2h; B) 32 g (0.32 mol) of hydrochloric acid was added to the above system,1.6 g (0.01 mol) of copper sulfate,Stirring until dissolved,Then 33.84 g (0.141 mol) of sodium bisulfite solution was added dropwise,After the addition was complete, the temperature was raised to 60 C. and incubated for 1.5 hours.The reaction is completed and extracted with methylene chloride, separated, the organic phase is dried, filtered, and the solvent is removed to give 2-chloro-6-trifluoromethylbenzenesulfonyl chloride;

The synthetic route of 433-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yellow River Delta Jingbo Chemical Institute Co., Ltd.; Yu Long; Yao Gang; Chang Jinlei; Chen Zhimin; Liu Kefeng; Fan Qiyan; (6 pag.)CN106478464; (2017); A;,
Chloride – Wikipedia,
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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. 6940-78-9 name is 1-Bromo-4-chlorobutane, 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. 6940-78-9

Methanol (149 L) , 7-hydroxy-lH-guinolin-2-one (14.87 kg), and potassium hydroxide (6.21 kg) were mixed in a reaction vessel, and the resulting mixture was stirred. After dissolution, l-bromo-4-chlorobutane (47.46 kg) was added thereto, and the resulting mixture was stirred under reflux for seven hours.Thereafter, the mixture was stirred at 10 C for one hour. The precipitated crystal was centrifuged and washed with methanol (15 L). The wet crystal was collected and placed in a tank. Water (149 L) was added thereto, followed by stirring at roomtemperature. After centrifugation, the result was washed with water (30 L). The wet crystal was collected and placed in a tank. After adding methanol (74 L), the mixture was stirred under reflux for one hour, cooled to 10 C, and then stirred. The precipitated crystal was centrifuged and washed with methanol (15 L). The separated crystal was dried at 60 C to obtain 7- (4- chlorobutoxy) -lH-quinolin-2-one (15.07 kg).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-chlorobutane, and friends who are interested can also refer to it.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; KANEKO, Daiki; MATSUDA, Takakuni; HOSHIKA, Yusuke; WO2013/162048; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2613-34-5, name is 3-Chloro-2,4-difluoroaniline, 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. 2613-34-5

1,3 -dimethyl-4-(N-(3 -methyloxetan-3 -yl)sulfamoyl)- 1 H-pyrrole-2-carboxylic acid (500 mg, 1.73 mmol), 3-chloro-2,4-difluoroaniline (0.57 g, 3.47 mmol) and HATU (0.88 g, 2.31 mmol) were dissolved in DMF (2 mL) containing DIPEA (0.69 mL, 3.98 mmol). The reaction mixture wasstirred at 65C for 28 hours and at room temperature for 60 hours. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 10 to 70%). The desired fractions were combined and evaporated to afford a light brown oil which solidified while standing. The solid was recrystallized from ethanol (5 mL) to afford a white solid which was filtered and washed with ethanol (1 mL). The white solid was dried overnight in vacuo,resulting in compound 243 (318 mg) as off white solid. Method D: Rt: 1.73 mm mlz: 432.0 (MH) Exact mass: 433.1 .?H NMR (400 MHz, DMSO-d6) oe ppm 1.52 (s, 3 H), 2.37 (s, 3 H), 3.73(s, 3 H), 4.11 (d, J=6.4 Hz, 2 H), 4.61 (d, J=5.9 Hz, 2 H), 7.35 (td, J=9.0, 2.0 Hz, 1 H), 7.47 (s, 1H), 7.67 (td, J=8.7, 5.8 Hz, 1 H), 7.91 (br. s., 1 H), 10.03 (br. s., 1 H).

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 2613-34-5.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 126764-17-8, name is 1-Chloro-6,6-dimethylhept-2-en-4-yne, I believe this compound will play a more active role in future production and life. 126764-17-8

29 kg of N-methyl-1 -naphthalene methylamine hydrochloride was charged into a reactor containing 70.4 liters of dimethylformamide and 11 liters of water, under stirring. The contents were stirred for 15 minutes for clear dissolution and 11 kg of sodium carbonate was added to it. The reaction mass was cooled to 13 EPO C and 22 kg of 1-chloro-6,6-dimethyl-2-heptene-4-yne was added slowly at 11 to 14 C. The reaction mixture was stirred at 12 to 14 0C for 60 minutes and then heated to 55 0C. The reaction mass was maintained at 60 C for 5 hours and reaction completion was confirmed by thin layer chromatography. The reaction mass was cooled to room temperature and 99 liters of water was added. Reaction mass was extracted three times with a total of 75 liters of dichloromethane (3×25 liters). Total organic layer was washed twice with 88 liters of water (2×44 liters); 18 liters of water was charged to the final organic layer and was cooled to 13 0C. Reaction mass pH was adjusted to 0.2 by adding 15 liters of 36% aqueous hydrochloric acid and stirring for 30 minutes. The organic layer was separated and washed three times with a total of 267 liters of water (3chi89 liters). Final organic layer was transferred into a reactor and the solvent was distilled completely below 45 C. 11.8 liters of petroleum ether was charged and the solvent distilled completely at below 50 C. Again 68 liters of petroleum ether was charged and heated to reflux. The mass was stirred at reflux for 30 minutes and cooled to 50 C. The solid thus formed was allowed to settle for 60 minutes and the top petroleum ether layer was decanted. The decantation process was repeated two more times. Finally 44 liters of petroleum ether was charged, heated to reflux, maintained for 30 minutes at reflux and then cooled to 25 C. The contents were stirred for 60 minutes at 20 to 25 0C and centrifuged to recover the solid. The centrifuged solid was washed twice with petroleum ether (2×16 liters) and spin- dried for about 60 minutes to get 29.3 kg of crude terbinafine hydrochloride as a semi-dry solid.

The chemical industry reduces the impact on the environment during synthesis 126764-17-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; DR. REDDY’S LABORATORIES, INC.; WO2007/44273; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 108-70-3, name is 1,3,5-Trichlorobenzene, I believe this compound will play a more active role in future production and life. 108-70-3

Example 4; Preparation method of 1,3,5-trifluorobenzene; 500 g of 1,3,5-trichlorobenzene, 1180 ml of sulpholane, 10.7 g of 3-nitrodimethylbenzamide and 640 g of dry KF were initially charged in an autoclave, then 48 g of CNC catalyst were added and the autoclave was sealed. The mixture was heated to 220 C. for 48 h. During the reaction, a maximum total pressure of 8 bar arose. Subsequently, the mixture was cooled to 20 C. The product was distilled off initially at standard pressure, later under reduced pressure. 310 g of a colourless liquid having a proportion of 87% by weight of 1,3,5-trifluorobenzene (74% of theory) and 8.8% by weight of difluorochlorobenzene (6.7% by weight of theory) were obtained. 1,3,5-Trifluorobenzene and difluorochlorobenzene can be separated distillatively in a known manner.

The chemical industry reduces the impact on the environment during synthesis 108-70-3. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pleschke, Axel; Marhold, Albrecht; US2006/9643; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 4863-91-6, name is 3-Chloro-5-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. 4863-91-6.

To a solution of compound 36.7 (1 eq) in toluene (50 eq) cooled in an ice water bath was added N,N,N’,N’-tetramethylethylenediamine (4 eq) and chlorotrimethylsilane (3 eq) the reaction mixture was allowed to come to rt for 30 min. Iodine (1.1 eq) was added portion wise at 10 C. After the addition of iodine was complete the reaction mixture stirred at RT for 3 h followed by diluting with EtOAc and washing with aq a2S204, dried over Na2SC>4 and concentrated in vacuo to afford to a residue. The crude iodo intermediate was dissolved in THF (19 eq) and added to a solution of 3-chloro-5-fluoroaniline (1 eq) in THF (40 eq) and sodium hydride (60% oil dispersion 1.2 eq). The reaction mixture was stirred at RT for 2 h followed by diluting with EtOAc and washing with 5% citric acid, dried over Na2SC>4 and the solvent removed in vacuo. The residue was purified by flash chromatography (10% EtOAc/Hexane to 100% EtOAc) to provide compound 36.8 (39% yield) as a white foam. EIMS (m/z): calcd. for C21H29CIFN3O4 (M++Na) 463.92, found 463.90.

The synthetic route of 3-Chloro-5-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; ERLANSON, Daniel, A.; MARCOTTE, Doug; KUMARAVEL, Gnanasambandam; FAN, Junfa; WANG, Deping; CUERVO, Julio, H.; SILVIAN, Laura; POWELL, Noel; BUI, Minna; HOPKINS, Brian, T.; TAVERAS, Art; GUAN, Bing; CONLON, Patrick; ZHONG, Min; JENKINS, Tracy, J.; SCOTT, Daniel; SUNESIS PHARMACEUTICALS, INC.; LUGOVSKOY, Alexey, A.; WO2011/29046; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

4863-91-6, Adding a certain compound to certain chemical reactions, such as: 4863-91-6, name is 3-Chloro-5-fluoroaniline, 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 4863-91-6.

2,5-Hexanedione (4.51 mL) and p-toluenesulfonic acid monohydrate (73 mg) were added to a solution of 3-chloro-5-fluoroaniline (5.12 g) in toluene (40 mL)-tetrahydrofuran (40 mL), and the mixture was heated under reflux for 3.5 hours. After being cooled down, the reaction solution was concentrated in vacuo, and the resultant residue was dissolved in chloroform. The solution was washed successively with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The resulted residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate = 97/3) to give the titled compound (7.63 g) as a yellow oil. APCI-MS m/z:224/226[M+H]+

According to the analysis of related databases, 4863-91-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Tanabe Pharma Corporation; EP2179994; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13726-14-2, A common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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.

Example 2(1-Benzyl-piperidin-4-yl)-(4-chloro-3-methoxy-phenyl)-amine/V-Benzylpiperidone (7.9 ml_, 43,8 mmol), 4-chloro-3-methoxy-phenylamine (6.9 g, 43.8 mmol) and sodium sulphate (31.1 g, 218 mmol) were suspended in dichloromethane (250 ml_). Sodium triacetoxyborohydride (11.4 g, 52.5 mmol) was added and the reaction mixture was stirred at room temperature overnight.Aqueous sodium hydrogencarbonate was added followed by stirring for 30 min.The mixture was extracted with dichloromethane and the combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo. (1 -Benzyl-piperidin-4-yl)-(4-chloro-3-methoxy-phenyl)- amine was precipitated from ethyl acetate/heptane 6.7 g (46%) as a white solid.

The synthetic route of 13726-14-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NEUROSEARCH A/S; WO2009/77585; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

118-69-4, 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 118-69-4 as follows.

step one:2,6-dichlorotoluene (100 g, 0.62 mol) was added to 1000 ml of dichloromethane at room temperature, and aluminum trichloride (165.6 g, 0.68 mol) was added thereto, and the temperature was controlled below 30 C.Acetyl chloride (97.5 g, 1.24 mol) was added dropwise to the reaction system at a rate of 20 drops per minute.After the completion of the dropwise addition, the temperature was raised to 40 C and refluxed for 12 hours.After the completion of the reaction, the reaction system was cooled to room temperature, and the reaction mixture was poured into 1000 ml of ice water, extracted with dichloromethane (500 ml ¡Á 3), and the organic phase was combined, washed with saturated brine (600 ml ¡Á 2), anhydrous sulfuric acid Magnesium is filtered after drying,The filtrate was concentrated under reduced pressure to give a red brown oil.106 g, crude yield was 84.2%.

According to the analysis of related databases, 118-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANDONG BESTCOMM PHARMACEUTICAL CO LTD; Shandong Bainuo Pharmaceutical Co., Ltd.; YU YANG; Yu Yang; CHEN JINGJIN; Chen Jingjin; ZHOU HUAYIN; Zhou Huayin; WANG LINYONG; Wang Linyong; ZHANG ZHIQIANG; Zhang Zhiqiang; SUN YUANJUN; Sun Yuanjun; QIU XIN; Qiu Xin; WANG YULIANG; Wang Yuliang; (16 pag.)CN108299480; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics