Formaldehyde → 3-(Hydroxymethyl)benzo[d]thiazol-2(3H)-one

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry containing 30.2 g (0.2 mol) of 2-hydroxybenzothiazole and 40 ml of methyl alcohol, 32 ml of 37% aqueous formaldehyde was added in one portion. The stirred mixture was heated at 78°-80° C. (reflux) for 30 minutes. At 80° C., 60 ml of hot water was added to the stirred solution. After cooling to 0° C., the product was collected by filtration, washed with 100 ml of heptane and air-dried at 25°-30° C. The product, 3-(hydroxymethyl)-2-benzothiazolinone, mp. 101°-3° C., was obtained in 94% yield. After recrystallization from isopropyl alcohol the melting point remained unchanged.

Provenance & Evidence