Pyridine → 5-(3-Methoxyacetyloxypropanesulfonyl)thiophene-2-sulfonamide

Participants

Reaction Steps

To a solution of 5-(3-hydroxypropane sulfonyl)thiophene-2-sulfonamide (1.2 g, 4.2 mmol) in 75 ml of THF was added 0.4 ml of pyridine and 0.5 g of methoxyacetyl chloride. The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The oily residue was dissolved in ethyl acetate and the ethyl acetate was washed with water and then brine. After drying over sodium sulfate the ethyl acetate was concentrated under vacuum, giving an oily residue. A crystalline product was obtained by dissolving the oil in hot dichloroethane and then cooling to 0° C. The yield was 0.8 g. m.p. 93°-95° C. 1H-NMR, δ (DMSO, d6) 8.00 (2H, s); 7.80 (1H, d, J=3); 7.63 (1H, d, J=3); 4.12 (2H, t, J=6); 4.00 (2H, s); 3.55 (2H, m); 3.27 (3H, s); 1.91 (2H, m).

Provenance & Evidence