Thiophosgene → HCID 89765672, compound

Participants

Reaction Steps

To a stirred solution of 3-chloro-4-(1-methyl-4,5-dihydro-1H-imidazol-2-ylsulfanyl)-phenylamine (5.0 g, 21 mmol) and diisopropylethylamine (5.37 g, 41.6 mmol) in dry tetrahydrofuran at 0° C. under N2 inert atmosphere, thiophosgene (2.39 g, 21 mmol) in tetrahydrofuran is added dropwise and stirred for 20 minutes. When the reaction is completed, the reaction mixture is concentrated at room temperature and taken in dichloromethane (100 mL), washed with water (2×50 mL) and dried over anhydrous MgSO4 to get the product as a brown solid (5.8 g, 99%). TLC: pet ether/ethyl acetate (8/2) Rf—0.4. LCMS (method A): mass found (M+H+, 282.0), Rt (min): 3.43, area % 71.5 (max); 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=2.16 Hz, 1H), 7.57 (s, 1H), 7.31 (m, 1H), 7.28 (m, 1H), 6.43 (d, J=8.56 Hz, 1H), 3.61 (s, 3H).

Provenance & Evidence