Hydroxyamine hydrochloride → 7-Bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime

Participants

Reaction Steps

To a solution of 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde (Example 5.3) (16.65 g) in ethanol (150 ml) were added hydroxylamine hydrochloride (9.52 g), sodium hydrogen carbonate (11.51 g) and water (15 ml). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with ethyl acetate (1500 ml) and water (400 ml). After separation of the phases, the aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water (200 ml) and brine (200 ml), dried over sodium sulfate and concentrated to give 7-bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde oxime (16.65 g) as a brown solid. 1H-NMR (DMSO-d6, 400 MHz): 11.94 (s, 1H), 8.66 (s, 1H), 8.09-9.90 (m, 2H) ppm.

Provenance & Evidence