Reaction #54482

Reaction equation

4-acetamido-2-bromothiazole

4-Acetamido-2-bromothiazole

methyl tosylate

sodium hydride

→

title compound

Yield 32.0%

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

Yield 32.0%

Solvents

—

oil

acetonitrile

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Otherthe filtrate evaporated under reduced pressure
3. 3
   OtherThe residue was chromatographed on silica (Woelm grade, 1, 150 g)
4. 4
   OtherEvaporation of the appropriate fractions
5. 5
   Otherfollowed by recrystallisation from hexane

Procedure

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%).

Source