Bromine → HCID 66898934, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4,4,4-trifluoro-butyramidine hydrochloride (2.1 g, 0.012 mol) in methanol (10 mL) at 0° C. under vigorous stirring was added dropwise bromine (0.61 mL, 0.012 mol) and a 5.4M sodium methylate solution in methanol (4.4 mL, 0.012 mol) simultaneously over 30 min maintaining a slight bromine excess by color. To the resulting nearly colorless suspension was added dropwise a solution of potassium thiocyanate (1.16 g, 0.012 mol) in methanol (10 mL) over 10 min at 0-10° C. The resulting mixture was stirred for 2 h at 0-10° C. and filtered. The isolated material was washed with methanol and dried which afforded a brown solid which was purified by flash chromatography (150 g silica gel 60 5% methanol/diethyl ether) and crystallized from diethyl ether/hexanes which afforded 3-(3,3,3-trifluoro-propyl)-[1,2,4]thiadiazol-5-ylamine (1.43 g, 61%) as a brown oil.

Provenance & Evidence