Nitric Acid → HCID 178432273, compound

Participants

Reaction Steps

5-Amino-2-methylbenzothiazole dihydrochloride (2.50 g, 10.54 mmol) was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated to afford the free base which was dissolved in ethanol (5 ml). A solution of cyanamide (660 mg, 15.71 mmol) in water (1 ml) was added followed by concentrated nitric acid (69%, 0.68 ml, 10.54 mmol) and the resulting mixture was refluxed for 18 h. The solid which formed on cooling to room temperature was collected and washed with cold ethanol then diethyl ether to give the title compound (1.36 g) as a beige solid m.p. 260-261° (dec.). δH (d6DMSO) 2.80 (3H, s), 7.26 (1H, m), 7.37 (4H, s), 7.78 (1H, s), 8.08 (1H, d, J 8.6 Hz) and 9.67 (1H, br s).

Provenance & Evidence