Tag: M.W=200-300

Electric Literature of 13918-92-8, The chemical industry reduces the impact on the environment during synthesis 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

General procedure: To 5-(5-(5-Aminopyridin-3-yl)thiophen-2-yl)-2-methyl- isoindolin-1-one (49) (225 mg, 0.79 mmol) in dry pyridine (23 mL) under N2 at RT,was added dropwise, 2,4-difluorobenzenesulphonyl chloride (336 mg, 1.58 mmol) in CH2Cl2(3 mL) over 5 min. The suspension was heated to 45 C under N2 for 4 h., at which pointanother portion of 2,4-difluorobenzenesulphonyl chloride (169 mg, 0.79 mmol) in CH2Cl2 (2mL) was added. The whole mixture was left to stir for at 45 C under N2 for 16 h., then thesolvent removed under reduced pressure. The resulting residue was suspended in acetone (10mL), 1 M HCl (20 mL) added, and the entire mixture stirred for 10 minutes. The solid wasthen collected by filtration, washed well with 1 M HCl and water, dried, and purified bychromatography as described below. In cases where the bis-sulphonamide was also formed, a second step was introduced wherethe crude product above was treated with a 1:1 mixture of 1,4-dioxane and 2 M NaOH. Thecrude sulphonamide resulting from subsequent acidification of the reaction mixture wasisolated by filtration, washed well with water, and dried. Purification was carried out by flashcolumn chromatography (2% MeOH/CH2Cl2 as eluant), giving the title compound as a paleyellow solid (211 mg, 545).

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, 2,4-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. HPLC of Formula: C8H9ClO2S

To a solution of 6-Amino-l-ethyl-4-methyl-4H-3,l-benzoxazin-2-one (0.140 g, 0.678 mmol) in ethyl acetate (5 mL) was added NN-diisopropylethylamine (0.175 g, 1.35 mmol) and p-tolylmethanesulfonyl chloride (0.180 g, 0.882 mmol). The reaction mixture was stirred for 15 min, concentrated and purified by flash chromatography to give the desired product as a pale solid (54 mg, 21 percent). LCMS : 0.92 min; ES+ 375 (M+H+); lH NMR (CHLOROFORM-d, 400MHz): delta (ppm) 7.12-7.20 (m, 4H), 7.09 (d, IH), 6.92 (d,lH), 6.89 (s, IH), 6.65 (s, IH), 5.29 (q, lH), 4.28 (s, 2H), 3.95 (q, 2H), 2.34 (s, 3H), 1.63 (d, 3H), 1.34 (t, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51419-59-1, its application will become more common.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; SYNGENTA PARTICIPATIONS AG; CUTLER, Sean, R.; LACHIA, Mathilde, Denise; WENDEBORN, Sebastian, Volker; GODFREY, Christopher, Richard Ayles; SABBADIN, Davide; (82 pag.)WO2018/17490; (2018); A1;,
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Synthetic Route of 41965-95-1,Some common heterocyclic compound, 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, molecular formula is C8H11Cl2NO, 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.

N,N-Diisopropylethylamine (4.0 mL, 22.9 mmol, 4.0 eq.) was added to a mixture of 28 (2.0 g, 5.23 mmol, 1.0 eq.) and (3-chloro-4-methoxyphenyl)methanamine hydrochloride [29] (1.8 g, 8.41 mmol, 1.6 eq) in n-propanol (40 mL). The resulting mixture was heated at reflux for 16 h. After cooling to room temperature, water (40 mL) was added to the reaction mixture. The formed precipitate was filtered, washed successively with water (20 mL) and ethanol (20 mL) and then dried in a desiccator to afford the desired product 29 (2.3 g, 4.44 mmol, 85%) as a white solid. Rf (SiO2, cyclohexane/ethyl acetate, 7/3, v/v): 0.48; Mp: 140-142 C; IR (cm-1): 1701 (nuC=O), 1320 (nuCF3), 1281 (nuC-O), 1110 (nuC-O), 1031 (nuC-O); 1H NMR (CDCl3, 400 MHz) delta 9.79 (brs, 1H, NH), 9.33 (s, 1H, H2), 8.41 (m, 1H, H5), 8.18 (d, 1H, 4JH7-H5 = 1.5 Hz, H7), 7.40 (d, 1H, 4JH2?-H6?= 2.2 Hz, H2?), 7.24 (m, 1H, H6?), 6.96 (d, 1H, 3JH5?-H6?= 8.5 Hz, H5?), 4.87 (d, 2H, 3JHd-NH = 5.9 Hz, Hd), 4.40 (q, 2H, 3JHb-Hc= 7.1 Hz, Hb), 3.92 (s, 3H, He), 1.41 (t, 3H, 3JHc-Hb= 7.1 Hz, Hc); 13C NMR (CDCl3, 100 MHz) delta 167.3 (Ca), 154.5 (C4), 154.1 (2C, C4?, C8a), 148.6 (C2), 131.1 (C1?), 130.2 (C2?), 129.6 (C6?), 127.9 (C7), 126.2 (C8), 125.2 (q, 2JC6-F = 33 Hz, C6), 123.8 (d, 1JCF3-F = 271 Hz, CF3), 123.4 (C3?), 121.6 (C5), 120.1 (C4a), 113.4 (C5?), 105.9 (C3), 61.5 (Cb), 56.6 (Ce), 49.9 (Cd), 14.4 (Cc); HRMS calculated for C21H1779Br35ClF3N2O3 [M+H]+ m/z 517.0141, found C21H1779Br35ClF3N2O3 [M+H]+ m/z 517.0150 (77%); C21H1781Br35ClF3N2O3 or C21H1779Br37ClF3N2O3 [M+H]+ m/z 519.0163 (100%); C21H1781Br37ClF3N2O3 [M+H]+ m/z 521.0134 (24%).

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

Reference:
Article; Liu, Jianrong; Maisonial-Besset, Aurelie; Wenzel, Barbara; Canitrot, Damien; Baufond, Ariane; Chezal, Jean-Michel; Brust, Peter; Moreau, Emmanuel; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 548 – 560;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

51419-59-1, name is p-Tolylmethanesulfonyl chloride, 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. COA of Formula: C8H9ClO2S

A solution of 1-(4-Amino-phenyl)-3-pyridin-4-ylmethyl-urea (80 mg, 0.33 mmol) in DIVIF (3 mL) was added p-Tolyl-methanesulfonyl chloride (94.7 mg, 0.46 mmol) and TEA (168.4 mg, 1.65 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was washed H20 (10 mL) and extracted with EA (50 mL). The combined organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by prep-HPLC (5-95; NH4HCO3) to give n- [4-(3 -pyridin-4-ylmethyl-ureido)-phenyl] -c-p-tolyl-methanesulfonamide (35 mg, yield 26percent) as a white solid. ?H NMR (400 IVIHz, DMSO-d6): oe = 9.49 (s, 1H), 8.68 (s, 1H), 8.51-8.49 (m, 2H), 7.37 (d, J 8.8 Hz, 2H), 7.28 (d, J 5.6 Hz, 2H), 7.18-7.13 (m, 4H), 7.08 (d, J= 8.8 Hz, 2H), 6.71 (t, J= 5.6 Hz, 1H), 4.32 (d, J 5.6 Hz, 2H), 4.29 (s, 2H), 2.29 (s, 3H). MS: m/z 410.9 (M+HH).

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

Reference:
Patent; SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INSTITUTE; GARDELL, Stephen; PINKERTON, Anthony B.; SERGIENKO, Eduard; SESSIONS, Hampton; (428 pag.)WO2018/132372; (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 1996-29-8 as follows. Safety of 1-Bromo-4-chloro-2-fluorobenzene

To a solution of 1-bromo-4-chloro-2-fluorobenzene (10.0 g, 47.8 mmol) in dry THF (300 ml.) at -78 C under nitrogen was added LDA (2.0 M solution in THF, 31 ml_, 62.1 mmol) dropwise and the mixture was stirred at -78 C for 15 min. DMF (7.00 g, 95.8 mmol) was added and the mixture was allowed to warm to room temperature. The reaction mixture was quenched with a saturated aqueous NH4CI solution and the mixture was extracted with EtOAc (400 ml. x 3). The combined organic extracts were washed with brine (300 ml_), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100% Pet. Ether) to give the title compound (4.0 g, 35%) as a white solid, which was used directly in the next step.

According to the analysis of related databases, 1996-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin, Joseph; CAMERINO, Michelle, Ang; WALKER, Scott, Raymond; STEVENSON, Graeme, Irvine; STUPPLE, Paul, Anthony; (266 pag.)WO2019/219820; (2019); 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 18282-59-2 as follows. Quality Control of 4-Bromo-1,2-dichlorobenzene

A. 1-Bromo-4,5-dichloro-2-nitro-benzene. 4-Bromo-1,2-dichlorobenzene (10.5 g, 46.3 mmol) was added to 25 mL concentrated sulfuric acid at 0° C. A 1:1 mixture of 70percent nitric acid and concentrated sulfuric acid (20 mL) was added dropwise over 40 min. The reaction mixture was allowed to warm to ambient temperature with stirring over 0.5 h, then was poured onto cracked ice. The resulting mixture was filtered through paper, and the collected solids were washed with water (5*) and then dried at 45° C. under reduced pressure for 30 min to provide 10.7 g of an 88:12 mixture of desired nitroarene to starting material. Recrystalization from absolute ethanol provided 4.76 g of long yellow needles corresponding to a 20:1 mixture of product to starting material. The mother liquor was concentrated and recrystallized twice to provide an additional 1.18 g of product (17:1 mixture with recovered starting material). TLC (silica gel, 1:1 hexanes/EtOAc): Rf=0.45. 1H NMR (400 MHz, CDCl3): 7.95 (s, 1H), 7.80 (s, 1H).

According to the analysis of related databases, 18282-59-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Allison, Brett; McAtee, Laura C.; Phuong, Victor K.; Rabinowitz, Michael H.; Shankley, Nigel P.; US2004/224983; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 63624-28-2, name is 2,4-Dimethoxybenzene-1-sulfonyl 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. Application In Synthesis of 2,4-Dimethoxybenzene-1-sulfonyl chloride

B) 3-(2-Chlorophenyl)-1-[(2,4-dimethoxyphenyl)sulphonyl]-5-methyl-3-[2-oxo-2-[4-(2-pyridyl)-1-piperazinyl]ethyl]-1,3-dihydro-2H-indol-2-one 0.0335 g of 60% sodium hydride in oil is added, at RT, to a mixture of 0.3 g of the compound obtained in the preceding step in 10 ml of THF, and the mixture is stirred for 30 minutes. 0.2 g of 2,4-dimethoxybenzenesulphonyl chloride is then added and the mixture is stirred at RT for 1 hour. 50 ml of water are added to the reaction mixture and the resulting mixture is extracted with EtOAc, the organic phase is dried over Na2SO4 and the solvent is evaporated off under vacuum.The residue is chromatographed on silica gel, eluding with a DCM/MeOH mixture (98/2; v/v).0.32 g of the expected product is obtained after crystallization from iso ether, m.p.=239 C.

The synthetic route of 2,4-Dimethoxybenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Di Malta, Alain; Garcia, Georges; Roux, Richard; Schoentjes, Bruno; Serradeil-Le Gal, Claudine; Tonnerre, Bernard; Wagnon, Jean; US2004/180878; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, 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 61881-19-4, SDS of cas: 61881-19-4

Disaccharide 92 (1.0 g, 1.03 mmol) was dissolved in a mixture of CH3CN/ /H20 (30 mL/7.5 mL). Ceric ammonium nitrate (1.69 g, 3.09 mmol) was added to the solution at 0 C and then the mixture was stirred at room temperature under N2 for 2 h. The mixture was concentrated to dryness and the residue was diluted with DCM (100 mL) and the organic phase was washed with H20 and then dried over Na2S04, filtered and the solvents were removed in vacuum. Silica gel column chromatography (3:2 hexanes-EtOAc) afforded the corresponding hemiacetal 93 (730 mg, 82%>). Compound 93, N-phenyltrifluoroacetimidoyl chloride (0.68 mL, 4.2 mmol) and DCM (50 mL) was cooled down to 0 C. DBU (127 mu, 0.95 mmol) was added and the mixture was stirred at room temperature for 1 h. The mixture was concentrated. Silica gel column chromatography (2: 1 hexanes-EtOAc) afforded the disaccharide donor 3 as a white solid (650 mg, 75%>).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; BOONS, Geert-Jan; WANG, Zhen; WO2012/135049; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 14862-52-3, name is 3,5-Dibromochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

General procedure: A mixture of 1,3-dibromo-5-chlorobenzene (2 g, 7.41 mmol), 9Hcarbazole(2.60 g, 15.56 mmol), tris(dibenzylideneacetone)dipalladium(339 mg, 0.37 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxy-1,1?-biphenyl (457 mg, 1.11 mmol) and sodium tert-butoxide (2.85 g,29.64 mmol) in 100 ml of toluene were heated at 80 C for 4 h underargon. After cooling down to room temperature, the mixture was extractedwith dichloromethane. The combined organic extracts weredried over Na2SO4 and evaporated under reduced pressure. The crudeproduct was purified by column chromatography on silica gel usingpetroleum ether/dichloromethane (PE/DCM, 8/1, v/v) as the eluent toafford the target compound (2.46 g, 75%).

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ran, Quan; Zhang, Yuan-Lan; Hua, Xiaochen; Fung, Man-Keung; Liao, Liang-Sheng; Fan, Jian; Dyes and Pigments; vol. 162; (2019); p. 632 – 639;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1008361-80-5, A common heterocyclic compound, 1008361-80-5, name is 4-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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 solution of 4-bromo-3-chlorobenzene-l,2-diamine (0.1 g) in DMF (2 mL) at room temperature Iota, Gamma-carbonyldiimidazole (0.110 g) was added. The resulting homogeneous solution was stirred overnight at room temperature and then poured into 20 mL of water. The title compound was isolated by filtration, washed with water containing a few drops of 2 N aq. HC1 and dried under high vacuum.

The synthetic route of 1008361-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics