Ethyl isocyanate → Methyl 4-(2-(3-ethylureido)thiazol-4-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(2-amino-1,3-thiazol-4-yl)benzoate (Intermediate 11; 150 mg, 0.64 mmol) in NMP (3 mL), ethyl isocyanate (90 μl, 1.14 mmol) was added. The solution was heated at 110° C. for one hour in a microwave. The crude was partitioned between water and EtOAc. The organic layer was washed with NaHCO3 solution, water and brine. It was dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (2% MeOH in DCM) to give the desired product (79 mg). MS (ESP): 306 (M+H+) for C14H15N3O3S; NMR: 1.06 (t, 3H), 3.12-3.16 (m, 2H), 3.85 (s, 3H), 6.48 (s, 1H), 7.66 (s, 1H), 7.98 (s, 4H), 10.65 (s, 1H).

Provenance & Evidence