2-Mercaptoethanol → 3-Fluoro-4-[(2-hydroxyethyl)sulfanyl]benzene-1-sulfonamide

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.11 g, 50% oil dispersion, 0.023 mol) was washed with petroleum ether then suspended in freshly degassed DMF (50 ml). 2-Mercaptoethanol (1.8 g, 0.023 mol) was added dropwise under nitrogen. When gas evolution ceased, N,N-Dimethyl-N'-(3,4-difluorobenzenesulfonyl)formamidine (5 g, 0.02 mol) was added and the mixture was heated in an oil bath about 2 hours (80° C.). DMF was removed in vacuo and the residue was treated with 100 ml of 10% NaOH. After an additional hour of stirring the solution was acidified with concentrated HCl and extracted with ethylacetate (2×100 ml), and dried over anhydrous magnesium sulfate. Removal of solvent left 3 g of a white solid which when recrystallized from butyl chloride had m.p.=109°-111° C.

Provenance & Evidence