Phosgene → HCID 178456956, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-amino-5-bromobenzenesulfonamide (0.8 g; 3.2 mmol) and potassium carbonate (0.54 g; 3.9 mmol) in acetone (20 ml) was added isopropyl isothiocyanate (0.387 g; 3.84 mmol). The mixture was heated to 60° C. and after 16 hr cooled, concentrated in vacuo and the crude residue was taken up in tetrahydrofuran (50 ml) and cooled to 0° C. To the cooled mixture was added triethylamine (0.648 g; 6.4 mmol) followed by the addition of phosgene in toluene 1.9M (1.82 ml) over 2 min. After 1 hr at 0° C. the mixture was concentrated in vacuo. The crude product was taken up in water (10 ml) and pH was adjusted to 6 with sodium bicarbonate. The precipitated product was collected by filtration and dried in vacuo at 50° C. for 16 hr giving 390 mg (38.3%) of the title compound; m.p. >220° C.

Provenance & Evidence