Phenyl thioxochloroformate → HCID 19434000, compound

Participants

Reaction Steps

A solution of the product from Step C (1.4 g, 4.05 mmol) and 4-dimethylaminopyridine (0.74 g, 6.08 mmol) in 1,2-dichloroethane (10 mL) were cooled in an ice bath. Phenyl chlorothionoformate (0.67 mL, 4.86 mM) was added slowly. The cooling bath was removed and the mixture was stirred at room temperature for 18 hr, mixed with 3:1 hexane/ethyl acetate (25 mL) and filtered through silica gel. The filtrate was concentrated and heated under vacuum (200° C./0.5 mm Hg) approximately 5 min followed by cooling the mixture to room temperature. The residue was purified by column chromatography (silica gel, 3:1 hexane/ethyl acetate to 7:3 methylene chloride/methanol) which gave 0.91 g (65%) of the desired product as an oil which was not purified further.

Provenance & Evidence