Triphenylphosphine → 2-(Aminomethyl)thiazole-4-carbonitrile

Participants

Reaction Steps

To a magnetically stirred solution of 2-azidomethyl-thiazole-4-carbonitrile (1.3 g, 7.8 mmol) in a mixture of THF (40 mL) and water (4 mL) was added triphenylphosphine (3.10 g, 11.8 mmol) portionwise with ice-bath cooling. After the addition was complete, the mixture was stirred for an additional 18 h at room temperature and extracted with 3% hydrochloric acid (10 mL). The resultant aqueous solution was extracted with ether, basified to pH=12 with 3N NaOH, extracted into ethyl acetate (3×), and the combined organic layers were washed with 100 mL of brine, dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 1.0 g (91%) of the title compound as an oil which was used in next step with out further purification.

Provenance & Evidence