Sodium Hydroxide → HCID 13393425, compound

Participants

Reaction Conditions

Reaction Steps

To ammonium hydroxide (14.8 M) (215 ml) were added dropwise simultaneously sodium hypochlorite solution (5.25%) (101 ml) and a solution of sodium hydroxide (2.75 g, 0.069 mole) and 6-(N-ethoxycarbonylamino)-2-mercaptobenzothiazole (17.50 g, 0.069 mole) in H2O (187 ml) with stirring at 5° C. After 1/2 hour the precipitated solid was collected by suction filtration and washed well with ice-H2O. The wet solid was suspended in acetone (284 ml) and treated dropwise with a solution of potassium permanganate (15.13 g, 0.092 mole) in H2O (284 ml) over an hour period maintaining the reaction temperature at 30° C. After stirring for an additional hour, the mixture was filtered to remove manganese dioxide, and the filtrate acidified with 12N HCl to precipitate the solid product. Chromatography on a silica gel column eluting with EtOAc:hexane (50:50 v/v) followed by crystallization from ethanol gave 500 mg of 6-(N-ethoxycarbonylamino)-2-benzothiazolesulfonamide, m.p. 223°- 224° C.

Provenance & Evidence