Methyl Isocyanate → 4-(5-Tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-(3-methylureido)thiazole

Participants

Reaction Steps

A reaction mixture comprising 3.0 g (0.01 mole) of 4-(5-tert-butyl-1,3,4-thiadiazol-2-ylcarbamoylmethyl)-2-aminothiazole, 50 ml of pyridine and 0.8 g (0.014 mole) of methyl isocyanate was heated at 35°-37° for four hours. The reaction solution was allowed to stand over the weekend at ambient temperature. Most of the pyridine was removed by employing a rotary evaporator. The residue was mixed with hexane and the crude solid was collected. The filter cake was well washed with ethyl acetate. There was obtained 2.5 g of product, m.p. 190° (dec.). N.M.R. (dimethyl-d6 sulfoxide) ∂ 1.4 [C(CH3)3 ], 2.6 (CH3, doublet), 3.7 (CH2), 6.7 (hetero-aromatic).

Provenance & Evidence