Phenyl Isothiocyanate → Ammonium Hydroxide

Participants

Reaction Steps

To a solution of the compound prepared in STEP B above (263 mgs, ca 1.0 mmol) in methylene chloride (10 mL) was added phenyl isothiocyanate (120 μL, 1.00 mmol). The resulting mixture was stirred at room temperature for 1 h, then treated with benzyltrimethylammonium tribromide (389.4 mgs 1.00 mmol). The resulting mixture was then stirred overnight. The reaction was quenched with aqueous sodium bicarbonate and the mixture extracted into methylene chloride. The organic layer was dried over sodium sulfate, then filtered and concentrated to yield a residue which was purified by normal phase column chromatography, eluting with 90:10:1 chloroform:methanol:concentrated ammonium hydroxide to yield (S)—N-(2-(benzo[d]thiazol-2-ylamino)ethyl)-2-(2,2,2-trifluoroacetamido)butanamide as a yellow solid.

Provenance & Evidence