2-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1) → HCID 58055096, compound

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Reaction Steps

To a suspension of 4-(chloromethyl)thiazol-2-amine hydrochloride (7.55 g, 41 mmol) in dichloromethane (150 mL) at 0° C. was added 3,4-dichlorobenzyl isocyanate (8.27 g, 41 mmol). A solution of DIPEA in dichloromethane (30 mL) was added over a period of 30 min and the mixture was stirred overnight at room temperature. Evaporation of the volatiles in vacuo followed by purification by column chromatography (EtOAc/heptane 1/1) afforded 1-(3,4-dichlorobenzyl)-3-(4-(chloromethyl)thiazol-2-yl)urea as an off-white solid (10.5 g, 30 mmol) in 73% yield. 1H-NMR (ppm, DMSO-d6): 10.80 (bs, 1H), 7.60 (d, 1H), 7.55 (s, 1H), 7.11 (t, 1H), 7.05 (s, 1H), 4.63 (s, 2H), 4.30 (d, 2H).

Provenance & Evidence