Acetyl chloride → HCID 10236818, compound

Participants

Reaction Steps

2-aminothiophenol (0.4 mmol) and PS-DIEA resin (0.35 g, 3.76 mmol/g) were combined in dichloromethane (4 mL) and agitated for 10 min. 5-chloro-6-(chloromethyl)-1,3-benzodioxole (0.3 mmol) was added and the reaction agitated for a further 3 h. Reaction was treated with MP BH4− resin (Argonaut 3.16 mmol/g) for 2 h then filtered. The filtrate was combined with triethylamine (0.4 mmol), PS-DMAP resin (0.1 g) and acetyl chloride (0.4 mmol). Agitate for 18 h then treat the reaction with PS-trisamine resin for 4 h, filter and remove the solvent under a stream of nitrogen. The residue was purified by reverse phase chromatography. 1H NMR (CDCl3) δ 8.38-8.32 (m, 2 H), 7.52 (m, 1 H), 7.38-7.32 (m, 1 H), 7.07-7.02 (m, 1 H), 6.83 (s, 1 H), 6.25 (s, 1 H), 5.93 (s, 2 H), 3.90 (s, 2 H), 2.09 (s, 3 H);MS (ESI+) for C16H14ClNO3S m/z 336 (M+H)+.

Provenance & Evidence