Water → N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide

HRID 619081Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)C(C)C)C.[CH3:33][O:34][CH2:35]Cl.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([N:13]([CH2:33][O:34][CH3:35])[S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)(=[O:16])=[O:15])[S:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.72 g of N-[4-(3-bromo-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide and 0.6 ml of ethyldiisopropylamine in 10 ml of methylene chloride was cooled to 0° C. and, after the addition of 0.13 ml of chloromethyl methyl ether, stirred at 0° C. for 2 h. Thereafter, the mixture was treated with 40 ml of water and extracted with methylene chloride. The organic phase was dried with magnesium sulphate and concentrated. After chromatography on 60 g of Kieselgel 60 with ethyl acetate/hexane (1:3) as the eluent the product-containing fractions were concentrated. 0.64 g of colorless N-[4-(3-bromo-phenyl)-thiazol-2-yl]-N-methoxymethyl-4-methyl-benzenesulfonamide, obtained in amorphous form, was processed without further purification.

Workup

extractionextracted with methylene chloride
dry with materialThe organic phase was dried with magnesium sulphate
concentrationconcentrated
concentrationAfter chromatography on 60 g of Kieselgel 60 with ethyl acetate/hexane (1:3) as the eluent the product-containing fractions were concentrated

Sources & evidence

ORD record: ord-b2b2da99014f41b1a414917b6ab57abc
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05958910

Reaction notes

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