Tag: M.W=100-200

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. 2106-04-9, name is 3-Chloro-2-fluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Chloro-2-fluoroaniline

Step 64.2: 5-r(3-Chloro-2-fluoro-phenylamino)-(4-chloro-2-methyl-phenyl)-1-isopropyl-2-(2- methoxy-phenyl)-1 H-imidazole-4-carboxylic acid methyl ester Intermediate D (620 mg, 1.45 mmol) was dissolved in DCM (15 mL). TEA (366 mg, 0.5 mL, 3.61 mmol) and MsCI (331 mg, 2.90 mmol) were added and the reaction mixture was stirred at rt for 6 h. All volatiles were removed under reduced pressure and the residual crude mesylate re-dissolved in DCM (10 mL). 3-Chloro-2-fluoro aniline (310 mg, 2.13 mmol) was added and stirring continued at rt for 16h. The solvent was evaporated under reduced pressure. EtOAc (10 mL) and TEA (0.5 mL) were added and the mixture stirred for 5 min at rt. The white precipitate was filtered off and the filtrate concentrated to give the crude product which was purified by flash chromatography (heptanes/EtOAc, 100:0? 1 :1 ) to give the title compound. tR: 1.42 min (LC-MS 2); ESI-MS: 556.3/558.3 [M+H]+ (LC-MS 2).

The synthetic route of 2106-04-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; FURET, Pascal; GUAGNANO, Vito; HOLZER, Philipp; KALLEN, Joerg; LIAO, Lv; MAH, Robert; MAO, Liang; MASUYA, Keiichi; SCHLAPBACH, Achim; STUTZ, Stefan; VAUPEL, Andrea; WO2013/111105; (2013); A1;,
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Electric Literature of 1939-99-7, These common heterocyclic compound, 1939-99-7, name is Phenylmethanesulfonyl 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.

Preparation 19: 3-Phenyl-l ,4,5-oxathiazepane 4,4-dioxide Step 1 : A/-(2-((Tert-butyldimethylsilyl)oxy)ethyl)- 1 -phenylmethanesulfonamide To a solution of 2-((tert-butyldimethylsilyl)oxy)ethanamine (11.7 g, 66.6 mmol) and triethylamine (11.2 mL, 79.9 mmol) in tetrahydrofuran (222 mL) at 0 C was slowly added phenylmethanesulfonyl chloride (12.7 g, 66.6 mmol) portion wise and the reaction was stirred at room temperature for 16 hours. MTBE was then added and the Et3N HCl salt was removed by filtration. The filtrate was then concentrated and purified by silica gel solumn chromatography (0-30% Acetone in heptane, 216 nM) to A^-(2-((tert-butyldimethylsilyl)oxy)ethyl)-l-phenylmethanesulfonamide (17.8 g, 81 % yield). LCMS (ESI), m/z, 330. [M+H] +.

The synthetic route of 1939-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; FAUBER, Benjamin; LADDYWAHETTY, Tammy; RENE, Olivier; (105 pag.)WO2016/96936; (2016); A1;,
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Reference of 7006-52-2, 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. 7006-52-2, name is N-Methyl-3-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In air, K2HPO4 (10 mol percent, 4.35mg), PMHS (242 mul), amine (0.25 mmol), formic acid (4.6equiv ,43.3mul), 18-crown-6 (20mol percent, 13.2mg) 4A MS(10mg) and 2 ml THF were added into a tube equipped with a water condenser. The reaction mixturewas stirred at 80C for 12 hours. The yields of isolated products were reported. The mixture was filtered through a silica gelcolumn with petroleum ether and ethyl acetate as the eluent. The resultant solution was concentrated and purified by silica gelcolumn chromatography to give the corresponding product.

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, N-Methyl-3-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huang, Yan; Deng, Wei; Lin, Bo-Lin; Chinese Chemical Letters; (2019);,
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Electric Literature of 452-83-5, The chemical industry reduces the impact on the environment during synthesis 452-83-5, name is 2-Chloro-5-fluoroaniline, I believe this compound will play a more active role in future production and life.

Nitrosonium tetrafluoroborate (802 mg, 6.87 mmol) was added to a solution of 2-chloro-5-fluoroaniline (1.00 g, 6.87 mmol) in acetonitrile (50 mL) at 0 C. The resulting mixture was stirred for 1 h, then diluted with ethyl ether (150 mL). The precipitate was filtered and air-dried to give 2-chloro-5-fluorobenzenediazonium tetrafluoroborate (1-1) as an off-white solid. 1H NMR (300 MHz, CD3OD) delta 8.66 (ddd, 1H, J=6.7, 2.1, 1.0 Hz), 8.16 (m1, 2H).

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

Reference:
Patent; Fraley, Mark E.; Garbaccio, Robert M.; Hartman, George D.; Hoffman, William F.; US2006/135594; (2006); A1;,
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Some common heterocyclic compound, 2613-32-3, name is 2-Chloro-4,5-difluoroaniline, molecular formula is C6H4ClF2N, 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. SDS of cas: 2613-32-3

Lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide (42 ml, 1 M solution in tetrahydrofuran, 42 mmol, CAS No 4039-32-1 ) was added drop wise within 5 minutes to a solution of 2-chloro-4,5-difluoroaniline (3.88 g, 23.2 mmol) in tetrahydrofuran (1 10 ml) at -78 C and the mixture was stirred for 1 h at that temperature. A solution of ethyl 4-{[tert-butyl(diphenyl)silyl]oxy}-1-(2-chloroethyl)cyclohexanecarboxylate (10.0 g, 21 .1 mmol) in tetrahydrofuran (1 10 ml) was added and the mixture was stirred for 2 h at -78(C. The mix ture was warmed to room temperature and stirred for 4 d. For work-up, the reaction mixture was added to a mixture of water and sodium bicarbonate solution and the mixture was extracted with ethyl acetate (3x). The combined organic phases were washed with sodium chloride, dried over sodium sulfate and concentrated under reduced pressure, the residue was purified by flash chromatography (340 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate). The product containing fractions were concentrated and were purified a second time by flash chromatography (120 g Snap cartridge, hexane/ethyl acetate gradient, 5% -> 25% ethyl acetate) to give the title compound in 2 fractions: fraction 1 (7.53 g, single isomer based on1H NMR, isomer 1, contains impurities from aniline and isomer 2), fraction 2 (1 .13 g, isomer 2). Fraction 1 (isomer 1 ):1H-NMR (400 MHz, DMSO-d6): delta [ppm] = 7.67-7.55 (m, 5H), 7.52-7.30 (m, 9H), 3.97 (br s, 1H), 3.60 (t, 2H), 2.15-2.07 (m, 2H), 2.04 (t, 2H), 1 .76-1 .63 (m, 2H), 1 .58-1 .45 (m, 2H), 1 .39-1 .27 (m, 2H), 1 .05 (s, 9H). LC-MS (Method 1 ): Rt= 1 .80 min; MS (ESIpos): m/z 518.3 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2613-32-3, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BUCHGRABER, Philipp; EIS, Knut; WAGNER, Sarah; SUeLZLE, Detlev; VON NUSSBAUM, Franz; BENDER, Eckhard; LI, Volkhart, Min-Jian; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philipp; (248 pag.)WO2018/78005; (2018); A1;,
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Application of 104-11-0, 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. 104-11-0 name is 1-(4-Chlorophenyl)-N-methylmethanamine, 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.

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
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Related Products of 39191-07-6, These common heterocyclic compound, 39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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 Step 1 intermediate (100 mg, 0.64 mmol) in THF (6.0 mL) at 0C were added triethylamine (195 mg, 1.93 mmol) and 4-nitrobenzoyl chloride (132 mg, 0.70 mmol). The mixture was stirred for 2 h at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL), washed with saturated aqueous sodium bicarbonate solution (20 mL)and saturated ammonium chloride solution (20 mL). The organic layer was washed with water (30 mL) and dried over anhydrous sodium sulfate. The residue thus obtained was purified by silica gel column chromatography to yield 152 mg of titled compound. ?H NMR (300 MHz,DMSO-d6): oe 2.82 (s, 3H), 2.94 (s, 2H), 7.38-7.44 (m, 5H), 7.68-7.77 (m, 3H).

The synthetic route of 39191-07-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; DAS, Sanjib; GHARAT, Laxmikant Atmaram; HARDE, Rajendra Laxman; THOMAS, Abraham; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; BAJPAI, Malini; (98 pag.)WO2017/199103; (2017); A1;,
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Reference of 102-49-8,Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: To a stirred solution of tosylate 1 (100 mg, 0.29 mmol) in Acetone or CHCl3 (3 mL) was slowly added amine 2 (0.58 mmol) and ketone 3 (0.87 mmol). Then p-TsOH (25 mg, 0.145 mmol)was addedto the reaction mixture. The resultant mixture was stirred at 60 C for 24 h until the reaction was completed as indicated by TLC. The reaction mixture was concentrated in vacuo, and then extracted with saturated aqueous NaHCO3 and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to give 4 or 5 as syrups.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Dichlorobenzylamine, its application will become more common.

Reference:
Article; Yuan, Wen; Xia, Jianhui; Zhang, Xiaoke; Liang, Peng; Zhang, Jichao; Jiao, Wei; Shao, Huawu; Tetrahedron; vol. 72; 27-28; (2016); p. 3994 – 4000;,
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Related Products of 57946-56-2,Some common heterocyclic compound, 57946-56-2, name is 4-Chloro-2-fluoroaniline, molecular formula is C6H5ClFN, 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.

A solution of 4-chloro-6-hydroxy-7-methoxyquinoline (3.0 g, 14 mmol) and 4-chloro-2-fluoroaniline (3.5 g, 23 mmol) in cyclohexanol (100 ml) containing 1M ethereal hydrogen chloride (16 ml) was heated at 155 C. for 18 hours.. After cooling the mixture was diluted with ether and isohexanes and the precipitate was collected by filtration.. The crude product was dissolved in a mixture of methylene chloride/methanol/ammonia (100/10/1) and silica (10 g) was added.. The solvent was removed by evaporation and the resulting powder was purified by flash chromatography eluding with methylene chloride/methanol/ammonia (95/5/1 increasing to 80/20/1) to give 4-(4-chloro-2-fluoroanilino)-6-hydroxy-7-methoxyquinoline (1.12 g, 25%). 1H NMR Spectrum: (DMSOd6) 3.95 (s, 3H); 6.30 (m, 1H); 7.25 (s, 1H);7.35 (m, 2H); 7.55 (m, 2H); 8.20 (d, 1H); MS (ESI): 319 [MH]+.

The synthetic route of 57946-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zeneca Limited; Zeneca Pharma S.A.; US6809097; (2004); B1;,
Chloride – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine 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 4584-46-7, Product Details of 4584-46-7

The experimental equipment used in this study was a Vapourtec R4/R2+ flow reactor. Stock A: Ginkgolide B (4.4g), acetonitrile (100mL). Stock B: DECH (2.15g), potassium iodide (0.332g), acetonitrile (90mL), water (10mL). Initially, two flows were pumped into micromixer LH 25. Upon mixing together, the mixture entered the packed bed microreactor filled with acid-binding agents. The total volume of the packed bed microreactor was 24.5mL. However, the remaining volume was 4.5mL when the microreactor was filled with calcium carbonate (2.5g). The volumetric flow rate of stock A/B was 0.75mL/min. That is to say, the residence time in the microreactor was 3min. Upon completion at a set temperature for the appropriate residence time, the obtained organic layer was concentrated under vacuum and further purified by column chromatography on silica gel (MeOH/CH2Cl2=1:50). Dimethylaminoethyl ginkgolide B: 1H NMR (DMSO-d6, 300MHz): delta 7.12 (s, 1H), 6.32 (s, 1H), 6.12 (s, 1H), 5.31 (d, 1H, J=3.6Hz), 5.12 (s, 1H), 4.54 (d, 1H, J=7.5Hz), 4.35-4.41 (m, 1H), 4.07 (d, 1H, J=7.2Hz), 3.55-3.59 (m, 1H), 2.81-2.88 (m, 1H), 2.57-2.64 (m, 1H), 2.32 (d, 1H, J=12.6Hz), 2.18 (s, 6H), 2.11-2.12 (m, 1H), 1.83-1.94 (m, 1H), 1.71-1.77 (m, 1H), 1.11 (d, 3H, J=6.9Hz), 1.04 (m, 9H). 13C NMR (DMSO-d6, 300MHz): delta 176.44, 173.02, 170.18, 109.59, 98.40, 92.78, 82.00, 78.62, 74.36, 74.00, 72.19, 67.52, 64.11, 57.44, 48.64, 43.71, 41.62, 40.09, 39.81, 39.53, 39.25, 38.98, 36.57, 31.75, 28.58. HRMS calcd. for C24H33NO10 496.2177 [M+H], found 496.2196.

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:
Article; Qin, Yin-Lin; He, Wei; Su, Mei; Fang, Zheng; Ouyang, Ping-Kai; Guo, Kai; Chinese Chemical Letters; vol. 27; 10; (2016); p. 1644 – 1648;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics