Methanol → Methyl 2-[(3-hydroxypropyl)sulfonyl]-5-sulfamoylbenzoate
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[C:16]([OH:18])=[O:17].OS(O)(=O)=O.[CH3:24]O>>[OH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:8][C:7]=1[C:16]([O:18][CH3:24])=[O:17]Participants
4
Procedure
4-(3-hydroxypropylthio)-3-carboxybenzene-sulfonamide (15 g, 0.0515 mol) and concentrated H2SO4 (4 ml) were dissolved in methanol (150 ml) and refluxed on a steam bath for about 5 hours. The solvent was removed and the residue was treated with water. The mixture was extracted with ethylacetate, which was washed with water, saturated sodium bicarbonate, water and brine. After drying, removal of the solvent left a tannish solid. Recrystallization from 1,2-dichloroethane gave 13.5 g of a white solid. M.p.=123°-125°.