Reacción #54482

Ecuación de reacción

4-acetamido-2-bromothiazole

4-Acetamido-2-bromothiazole

methyl tosylate

sodium hydride

→

title compound

Rendimiento 32.0%

2-Bromo-4-(N-methylacetamido)thiazole

Rendimiento 32.0%

Disolventes

—

oil

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtered
2. 2
   Otrothe filtrate evaporated under reduced pressure
3. 3
   OtroThe residue was chromatographed on silica (Woelm grade, 1, 150 g)
4. 4
   OtroEvaporation of the appropriate fractions
5. 5
   Otrofollowed by recrystallisation from hexane

Procedimiento

A solution of 4-acetamido-2-bromothiazole (prepared as described in Example 1) and methyl tosylate (4.65 g, 25 mM) in dry acetonitrile (125 ml) was treated with a 60% dispersion of sodium hydride in oil (1 g, 25 mM) and the mixture stirred 72 hours at ambient temperature. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. The residue was chromatographed on silica (Woelm grade, 1, 150 g) using 2% methanol in chloroform as eluant. Evaporation of the appropriate fractions followed by recrystallisation from hexane gave the title compound (1.9 g, 32%) mp 84° C. Found: C, 30.55; H, 2.95; N, 11.8%. C6H7N2BrOS requires C, 30.7; H, 3.0; N, 11.9%).

Fuente