Phenyl isocyanate → HCID 23372942, compound

Participants

Reaction Conditions

Reaction Steps

nBuLi (1.8 ml, 2.34M) was slowly added to a solution of N-(3,4-dimethyl-5-isoxazolyl)pyridine-2-sulfonamide (500 mg, 2.0 mmol) in THF (14 ml) at -78° C. The mixture was stirred at -78° C. for 1 hour. Phenylisocyanate (3.55 mg, 2.9 mmol) was then added slowly and the mixture was allowed to warm room temperature. The reaction was quenched with H2O and the volatiles were removed under reduced pressure. The aqueous residue was extracted with EtOAc (2×50 ml). The aqueous layer was acidified with concenrated HCl to pH 4(~50 ml) and extracted with EtOH (2×50 ml). The combined organic layer was dried (MgSO4), filtered and evaporated to give a yellow oil, which was purified by HPLC to give an 88% yield with a m.p. of 199°-200° C.

Provenance & Evidence