Hydrogen Bromide → 2-Bromo-5-tert-butyl-1,3,4-thiadiazole

Participants

Reaction Conditions

Reaction Steps

48% Aqueous hydrobromic acid (67.5 ml) was added to a solution of 2-amino-5-t-butyl-1,3,4-thiadiazole (43 g) in glacial acetic acid (300 ml) the mixture was warmed to 65° C. and a solution of sodium nitrite (56 g) in water (80 ml) was added dropwise with stirring over 60 minutes at 65°-75° C. The mixture was cooled to 20° C. and was poured into water. The organic layer was extracted into ether (2×300 ml) and the extracts were combined, washed with sodium bicarbonate solution until neutral and dried over magnesium sulphate. The drying agent was filtered off and the solvent was evaporated to give a yellow oil which was distilled under reduced pressure to give 2-bromo-5-t-butyl-1,3,4-thiadiazole (47 g, 78%) as a colourless liquid, bp 134°-136° C. at 23 mm Hg.

Provenance & Evidence