N'-(3-butyl-5-tert-butyl-1,3,4-thiadiazol-3-ium-2-yl)-N,N-dimethylmethanimidamide bromide → 5-Tert-butyl-3-butyl-1,3,4-thiadiazol-2(3h)-imine

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Reaction Steps

A solution of Example 162B (4 g, 11.45 mmol) in 1N HCl (12.6 mL) was heated at 65° C. for 12 hours. The mixture was cooled at room temperature and extracted with ether (2×20 mL). The aqueous phase was neutralized to pH 7 with concentrated ammonia and extracted with ether (2×25 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on SiO2 using an Analogix® Intelliflash280™ (Hexanes-EtOAc: 0-80%) to give the title compound. LC/MS m/z 214 (M+H)+.

Provenance & Evidence