2-(Methylamino)ethanol → 5-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-ethyl)-methyl-amide

Participants

Reaction Steps

A suspension of 2-(methylamino)-ethanol (0.29 g, 3.86 mmol) and magnesium oxide (0.77 g, 19.1 mmol) in THF (4 ml) and water (1.4 ml) was allowed to stir at room temperature for 30 min, 5-chloro-4-nitrothiophene-2-sulfonyl chloride (1.0 g, 3.81 mmol) dissolved in THF (1.6 ml) was added drop wise at room temperature over a period of 1 h and the reaction mixture was allowed to stir for an additional hour. Filtration over Decalite and evaporation yielded the crude product which was further purified by flash chromatography on silica gel (ethyl acetate/heptane) to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-ethyl)-methyl-amide (0.4 g, 35%) as a yellow solid. MS (EI) 300.0 [(M)+], mp 62° C.

Provenance & Evidence