Methyl p-toluenesulfonate → 2-bromo-4-(N-methylacetamido)thiazole

HRID 26204Notes

Reaction equation

HRID 26204 reaction equation
[C:1]([NH:4][C:5]1[N:6]=[C:7]([Br:10])[S:8][CH:9]=1)(=[O:3])[CH3:2].S(C1C=CC(C)=CC=1)(O[CH3:15])(=O)=O.[H-].[Na+]>C(#N)C>[Br:10][C:7]1[S:8][CH:9]=[C:5]([N:4]([CH3:15])[C:1](=[O:3])[CH3:2])[N:6]=1

Participants

5

Reactant 3

HCID 6645Methyl p-toluenesulfonateHCID 24758Sodium hydrideHCID 202940434-Acetamido-2-bromo-thiazole

Product 1

HCID 203771682-bromo-4-(N-methylacetamido)thiazoleYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure
  3. customThe residue was chromatographed on silica (Woelm grade, 1, 150 g)
  4. customEvaporation of the appropriate fractions
  5. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-b77032338537498ca06597cc4eb4f8a0
Source dataset
uspto-grants-1979_04
Patent number
US04148904

Reaction notes

Loading…