Acetyl chloride → p-Acetamidophenyl methyl disulfide

Participants

Reaction Steps

To a solution of 39a (50 mg, 0.3 mmol) in dry CH2Cl2 (3 ml) was added triethylamine (127 μL, 0.9 mmol, 3 eq.), followed by acetyl chloride (32 μL, 0.45 mmol). The reaction was stirred at RT for 1 hr., then was diluted with dichloromethane, washed with water, then 5% aq. HCl, then 5% aq. NaHCO3. Dried over MgSO4, then concentrated in vacuo to give a yellow oil which solidified on standing. Chromotography (1:1 petroleum ether:ethyl acetate) gave 18 mg (29%) as a light brown solid. 1H NMR (400 MHz, CDCl3): δ 7.47 (s, 4H); 2.41 (s, 3H); 2.16 (s, 3H).

Provenance & Evidence