Triethylamine → N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2,3-dichlorophenyl)carbodiimide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2,3-dichlorophenyl)thiourea (270 mg, 0.45 mmol) in dichloromethane (10 mL) at 0° C., methanesulfonyl chloride (0.07 mL, 0.9 mmol) and triethylamine (0.13 mL, 0.9 mmol) were added. 4-Dimethylaminopyridine was added as a catalyst. The reaction mixture was stirred at 0° C. for 1 hour, then it was partitioned between dichloromethane and water. The combined organic phase was dried and concentrated to give the desired product (270 mg, crude). 1H NMR (CDCl3) δ 0.47 (s, 6H), 1.05 (s, 9H), 2.9 (s, 6H), 7.08 (d, 1H), 7.12 (d, 1H), 7.2 (t, 1H), 7.31 (m, 2H).

Provenance & Evidence