Hydrochloric Acid → 2-Bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carboximidamide

Participants

Reaction Conditions

Reaction Steps

2.5 M n-Butyllithium in hexanes (1.20 mL, 2.99 mmol) was added dropwise to a solution of hexamethyldisilazane (0.61 mL, 2.9 mmol) in diethylether (5 mL) at 0° C. The mixture was stirred for 30 mins at 0° C. and 2-bromo-4-(2,4-dichlorophenyl)-1,3-thiazole-5-carbonitrile (400 mg, 1.0 mmol) in THF (50 mL) was added. After stirring at rt for 2 hours LCMS indicated complete conversion. The reaction mixture was poured to a cold 2N HCl (10 ml) and was extracted with diethylether (2×20 mL). The aqueous phase was adjusted to pH˜10 with NH4OH and was extracted with DCM (3×30 mL). Combined DCM extracts were dried over Na2SO4, filtered and evaporated under reduced pressure to afford the title compound which was used directly in the next step (0.360 g, 80%). LCMS: (FA) ES+, 350, 352, 354.

Provenance & Evidence