Tag: M.W=100-200

Application of 33353-68-3,Some common heterocyclic compound, 33353-68-3, name is 3,5-Dichloro-2-methoxyaniline, molecular formula is C7H7Cl2NO, 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.

6,8-Dichloro-5-methoxy-2H-benzorein ,2,41thiadiazin-3(4H)-one 1 ,1 -dioxide (lnt-24) A 250 mL round-bottomed flask was charged with chlorosulfonyl isocyanate (0.717 ml) in nitropropane (40 ml) to give a colorless solution at -40 C under nitrogen. After 10 min, a solution of 3,5-dichloro-2-methoxyaniline (1220 mg) in nitropropane (20 ml) was added to the reaction mixture. After 10 min, the reaction was warmed to 0 C. After 30 min, aluminum chloride (1 101 mg) was added to the reaction mixture. After 5 min, the reaction mixture was warmed to 100 C. After 45 min, the reaction mixture was poured in ice/water (400 mL) and stirred for 1 h. The solids were filtered and washed with water and hexanes, and dried in a vacuum oven overnight to obtain the titled compound (391 mg). LCMS m/z 297.1 (M+H).

The synthetic route of 33353-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ADAMS, Jerry Leroy; ATOR, Laura E.; DUFFY, Kevin J.; GRAYBILL, Todd L.; KIESOW, Terence John; LIAN, Yiqian; MOORE, Michael Lee; RALPH, Jeffrey M.; RIDGERS, Lance Howard; (370 pag.)WO2017/98421; (2017); A1;,
Chloride – Wikipedia,
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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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 3-Chloro-5-trifluoromethylaniline

To a solution of 3-Chloro-5-trifluoromethyl-aniline (425 mul, 3.1 mmol, 1.03 eq.) in dry THF (15 ml) was added 4-Chloro-3-(trifluoromethyl)-phenylisocyanate (665 mg, 3.0 mmol). After stirring overnight at rt the mixture was diluted with cHexane (100 ml), washed twice with 2 N HCl, once with sat. NaHCO3 and brine (100 ml each) and adsorbed on Celite in vacuo. Flash chromatography on silica with cHexane/TBME (4:1 to 2:1) yielded 952 mg product (76%) as a white powder. 1H NMR (DMSO) delta 9.43 (s, 2H), 8.10 (d, J=2.5 Hz, 1H), 7.84 (m, 2H), 7.69 (dd, J=9.0, 2.5 Hz, 1H), 7.64 (d, J=9.0 Hz, 1H), 7.45 (s). MS (ES-): 414.9.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arpida AG; US2009/23813; (2009); 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 928-50-7 as follows. Product Details of 928-50-7

Equipped with a mechanical stirrer, a reflux condenser and a thermometer 1000ml four-necked flask, followed by adding 50g (0.48mol) 5- chloro-1-pentene, 50g (0.27mol) phthalimide potassium salt, triphenyl phosphine bromide 0.25g, 2.5g and 500g of nickel sulfate, hexamethylphosphoric triamide. After the addition was complete, the oil bath was heated to 200 deg.] C, the reaction was kept for 3 hours. After incubation, cooled to room temperature. Filter cake by-product potassium chloride reactions, polymerization inhibitor and a catalyst. Rinsed with acetone 100ml fresh cake combined filtrate and washings. Under reduced pressure using a rotary evaporator, acetone was distilled off spin, hexamethylphosphoric triamide and the excess of 5-chloro-1-pentene. Get 57g red viscous liquid, liquid chromatography measured content of 94.81%, the yield was 98.09%.

According to the analysis of related databases, 928-50-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yizheng Haifan Chemical Co., Ltd; Zou, Congwei; (9 pag.)CN106008314; (2016); A;,
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These common heterocyclic compound, 7051-15-2, name is 2-Chloro-1,3-dimethoxybenzene, 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. Recommanded Product: 2-Chloro-1,3-dimethoxybenzene

The 13.9g acetophenone (115.6mmol), 10.9g chlorobenzene (96.7mmol), 11.1g sodium tert-butoxide (115.6mmol) and 0.35g azacarbene imine palladium catalyst added in Example 6 9.8g p-cyanoacetophenone (67.3mmol), 9.6g 2,6-dimethoxychlorobenzene (56.1mmol), 6.5g sodium tert-butoxide (60mmol) and 0.2g azacyclocarbene imines The palladium catalyst and 60 mL of 1,4-dioxane solvent were not changed under other conditions, and the target product was obtained 14.0 g, and the isolated yield was 89%.In Example 6, the 0.35g nitrogen heterocyclic carbene imine palladium catalyst A1 was replaced with 0.24g A2, 0.29g A3, 0.34g A4, 0.24g A5, and the separation yields were 98%, 96%, 90%, 90%.

The synthetic route of 2-Chloro-1,3-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Chemical Institute Co., Ltd.; Lu Huiyang; Shen An; Cao Yucai; Li Yongqing; Ni Chen; Hu Yucai; (14 pag.)CN110818545; (2020); A;,
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Reference of 25186-47-4, A common heterocyclic compound, 25186-47-4, name is 3,5-Dichlorotoluene, molecular formula is C7H6Cl2, 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 stirred solution of l ,3-dichloro-5-methylbenzene (2.0 g, 12.4 mmol) in THF (20 mL) was added n-BuLi (2.0 M in hexane, 9.3 mL, 18.6 mmol) at -78 C dropwise over a period of 10 miri and mixture was stirred at -78 C for 30 min. A dry-ice was added to the reaction mixture slowly and the mixture was stirred at the same temperature for 20 min. Thereafter, the reaction mixture was slowly warmed to room temperature, quenched with 6 M HC1 (10 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure to get compound Al 11 -1 (1.1 g, 44%) as a white solid.

The synthetic route of 25186-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEIJIN PHARMA LIMITED; AMGEN INC.; BECK, Hilary Plake; BOOKER, Shon Keith; BREGMAN, Howard; CEE, Victor J.; CHAKKA, Nagasree; CUSHING, Timothy D.; EPSTEIN, Oleg; FOX, Brian M.; GEUNS-MEYER, Stephanie; HAO, Xiaolin; HIBIYA, Kenta; HIRATA, Jun; HUA, Zihao; HUMAN, Jason; KAKUDA, Shinji; LOPEZ, Patricia; NAKAJIMA, Ryota; OKADA, Kazuhisa; OLSON, Steven H.; OONO, Hiroyuki; PENNINGTON, Lewis D.; SASAKI, Kosuke; SHIMADA, Keiko; SHIN, Youngsook; WHITE, Ryan D.; WURZ, Ryan P.; YI, Shuyan; ZHENG, Xiao Mei; WO2015/129926; (2015); A1;,
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Related Products of 90390-33-3, 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. 90390-33-3 name is 3-Chloro-5-fluorobenzylamine, 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.

Weigh 159 mg of 3-chloro-5-fluorobenzylamine (1 mmol) in a dry 50 mL eggplant-shaped reaction flask, add 15 mL of dichloromethane, and stir until the substrate is completely dissolved.After adding 200 muL of triethylamine, 192 mg of (E) oct-6-enoyl chloride (1.2 mmol) dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.The mixture was separated by silica gel column chromatography under reduced pressure to give (E)-N-(3-chloro-5-fluorobenzyl)oct-6-enamide.

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

Reference:
Patent; Shanghai Shidande Biological Co., Ltd.; Shanghai Shidande Criterion Technology Services Co., Ltd.; Qian Yong; Xin Zhenqiang; Shu Yaping; Zhang Tianyong; Xie Tianpei; (11 pag.)CN108503559; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6480-66-6,Some common heterocyclic compound, 6480-66-6, name is 2,6-Dichloro-4-methoxyaniline, molecular formula is C7H7Cl2NO, 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.

Trichloromethyl carbonochloridic acid ester (0.0065 mol) was added to the solution of 2,6-dichloro-4-methoxybenzenamine (0.001 mol) and Et3N (0.4 ml) in dry toluene (16 ml). The reaction mixture was stirred for 2 hours at 6O0C till the starting aniline reacted completely (control by TLC). Then, a solution of intermediate 24 (prepared according to A8.c) in DCM (4 ml) was added to the reaction mixture at 6O0C at stirring. Formation of precipitate was observed. The stirring was continued at 60-70C for 1 hour. Then, the reaction mixture was concentrated in vacuum. The formed sediment was treated with water and filtered off. Then, it was washed with water, ethyl acetate, ether, and dried on the air. Yield: 0.360 g of compound 15 (66 %).

The synthetic route of 6480-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/148868; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 41332-02-9,Some common heterocyclic compound, 41332-02-9, name is 1-(2-Chloroethyl)naphthalene, molecular formula is C12H11Cl, 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: An aqueous solution of [18F]F- (0.5-3.5 mL, flow rate 0.5-30 mL/min) was passed through the column (borosilicate glass tubing, ID 4 mm, OD 0.6 cm, length 12 cm) packed with the resin (5-500 mumol; glass beads to fill the remaining volume). To remove the bulk of water, the column was flushed with He(gas) (flow rate 100 mL/min, 3 min). The column was dried by passing MeCN oracetone (1-10 mL, flow rate 1.5-20 mL/min) through, followed by a helium flush (100 mL/min,2-5 min). The column was primed by passing the radiofluorination solvent (MeCN for mannosetriflate, MeCN/tBuOH 1:5 for FLT-ONs, toluene for the naphthalene derivatives and 2-nitro-3-methoxypyridine, dry, 4 mL, flow rate 2 mL/min) through the column at room temperature followed by the substrate (50-100 mumol) dissolved in the radiofluorination solvent (dry, 3 mL) at 60-120 C (flow rate 0.55 mL/min). The radiofluorination solvent (dry, 2 mL, flow rate 0.55 mL/min) was then passed through the column again to elute the remaining product. The reaction mixture was analyzed by radio-TLC (eluent heptane:EtOAc 80:20 for the naphthalene derivatives, MeCN:H2O 95:5 for FDG, DCM:MeOH 9:1 for hydrolyzed FLT, petroleum ether:EtOAc 3:1 for the pyridine derivative. Total timeof radiosynthesis was 35-45 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(2-Chloroethyl)naphthalene, its application will become more common.

Reference:
Article; Mathiessen, Bente; Zhuravlev, Fedor; Molecules; vol. 18; 9; (2013); p. 10531 – 10547;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 29027-17-6, The chemical industry reduces the impact on the environment during synthesis 29027-17-6, name is 2-Chloro-3-methylaniline, I believe this compound will play a more active role in future production and life.

a (2-Chloro-3-methyl-phenyl)-hydrazine The title compound was prepared in accordance with the general method of example 25a) from 2-chloro-3-methylaniline.

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-Chloro-3-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bentley, Jonathan M.; Hebeisen, Paul; Muller, Marc; Richter, Hans; Roever, Stephan; US2002/35110; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 33050-36-1, 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. 33050-36-1 name is 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, 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.

3-Mercapto-s-triazolo[4,3-b]pyridazine A mixture of 1.20 g. (8 mmole) of 3-chloro-s-triazolo[4,3-b]pyridazine [P. Francavilla and F. Lauvia, J. Het. Chem., 8, 415 (1971) and 120 g. (16 mmole) of KSH in 20 ml. of ethanol was heated for 8 hours at 130 in a sealed tube. After cooling the mixture was evaporated to dryness and the residue was dissolved in 100 ml. of water, treated with active carbon, acidified to pH 1 with dil. HCl to precipitate 3-mercapto-s-triazolo[4,3-b]pyridazine which was collected, washed with 10 ml. of water and dried in vacuo over P2 O5 to yield 0.75 g. (62%), m.p. 260-270 (dec.). IR: nu maxKBr 3080, 2940, 2760, 1620, 1500, 1280, 1055 cm-1. NMR: ? ppmDMSO-d6 6.99 (1 H, d-d, 4 & 10 Hz, 7-H), 7.67 (1 H, d-d, 2 & 10 Hz, 8-H), 8.15 (1 H, d-d, 2 & 4 Hz, 6-H), 12.3 (1 H, br-s, disappear by addition of D2 O). Anal. Calcd. for C5 H4 N4 S. 1/2H2 O: C, 37.26; H, 3.13; N, 34.76. Found: C, 37.35; H, 2.32; N, 34.81.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-[1,2,4]triazolo[4,3-b]pyridazine, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Company; US3946000; (1976); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics