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

HRID 2419325Notes

Reaction equation

HRID 2419325 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 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. Evaporations of the appropriate fractions followed by recrystallisation from hexane gave 2-bromo-4-(N-methylacetamido)thiazole (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. customEvaporations of the appropriate fractions followed by recrystallisation from hexane

Sources & evidence

ORD record
ord-0e6177a085d14aae9e36264aadc3c510
Source dataset
uspto-grants-1978_08
Patent number
US04105773

Reaction notes

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