Hydrochloric Acid → HCID 19026921, compound

Participants

Reaction Steps

Diethylcarbamoyl chloride (1.49 ml; 11.3 mmol) was added to cyclobutylmethyl 1,2,4-triazol-3-yl sulfone (2.06 g; 10.2 mmol) in dry pyridine (10 ml) under dry nitrogen, and the solution stirred at room temperature overnight. The reaction mixture was poured into cold 2M hydrochloric acid (60 ml) and the cloudy solution extracted with two portions of ethyl acetate (120 ml and 50 ml). The extracts were combined, washed with saturated brine (50 ml), dried (Na2SO4), filtered and the volume of solution reduced by evaporation until a white solid precipitates. Hexane was added to the mixture which was then cooled and the solid filtered off to afford 3-(cyclobutylmethylsulfonyl)-N,N-diethyl-1,2,4-triazole-1-carboxamide (2.40 g; 78%) as white crystals, m.p. 113°-116° C., (Found, C: 47.96; H: 6.56; N: 18.51; S: 10.85. C12H20N4O3S requires C: 47.98; H: 6.71; N: 18.65; S: 10.67%). NMR - d(CDCl3 ; 60 MHz) 1.3 (6H, t, J=7 Hz), 1.5-2.4 (6H, m), 2.4-3.2 (1H, m), 3.4-3.8 (6H, m) and 8.9 (1H, s). IR vmax (CHCl3) 3000, 1710, 1440, 1340, 1270, 1180, 1145, 1030 and 870 cm-1.

Provenance & Evidence