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

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%).

1. customAfter 1 h the mixture was evaporated to dryness
2. concentrationthe mixture was concentrated
3. custom(rotary evaporator)
4. custompartitioned between dichloromethane and brine
5. extractionThe organic extract
6. washwas washed with half-saturated brine
7. customdried
8. customevaporated
9. filtrationTrituration with petroleum ether, filtration
10. customdrying in vacuo (CAUTION—no heating)

ORD-Eintrag

ord-b31ca04aedc04f8c9576af47f52ccc69

Quelldatensatz

uspto-grants-2003_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06638953B2