Reaktion #54482

Reaktionsgleichung

4-acetamido-2-bromothiazole

4-Acetamido-2-bromothiazole

methyl tosylate

sodium hydride

→

title compound

Ausbeute 32.0%

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

Ausbeute 32.0%

Lösungsmittel

—

oil

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle