Water → 2-(3-Pyridinyl)-4-thiazolylcarbonylazide

Participants

Reaction Steps

A suspension of 2-(3-pyridyl)-thiazolecarboxylic acid (0.824 g, 4 mmol) in dichloromethane-chloroform (30 ml-15 ml) was treated with triethylamine (0.75 ml, 0.5 g, 5 mmol) and then dibutyl chloroformate (0.65 ml, 0.68 g, 5 mmol). After 1 h the mixture was evaporated to dryness and the residue suspended in THF (30 ml) and a solution of sodium azide (0.46 g, 7 mmol) in water (10 ml) was added. After 1 h, the mixture was concentrated (rotary evaporator) and partitioned between dichloromethane and brine. The organic extract was washed with half-saturated brine, dried, and evaporated. Trituration with petroleum ether, filtration, and drying in vacuo (CAUTION—no heating) afforded the title compounds as a brown solid (0.37 g, 40%).

Provenance & Evidence