Imidazole → N-[4-Chloro-2-tert-butyldimethylsilyloxy-3-(N'',N''-dimethylaminosulfonyl)phenyl]-N'-(2-bromophenyl)thiourea

Participants

Reaction Steps

To a solution of N-[4-chloro-2-hydroxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-bromophenyl)thiourea (500 mg, 1.07 mmol) in THF (20 mL), tert-butyldimethylsilyl chloride (810 mg, 5.35 mmol) and imidazole (144 mg, 2.14 mmol) were added. The reaction mixture was stirred at room temperature for 16 hours. Then it was partitioned between ethyl acetate and water. The combined organic phase was dried and concentrated. Chromatography of the residue on silica gel (30% Ethyl acetate/Hexane) gave desired product (240 mg, 40%) and recovered starting material (280 mg). EI-MS m/z 580 (M+).

Provenance & Evidence