Methyl p-toluenesulfonate → HCID 20377168, compound

HRID 2052219Notes

Reaction equation

HRID 2052219 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 20377168HCID 20377168, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-acetamido-2-bromothiazole (prepared as described in Example 1) and methyl tosylate (4.65g, 25mM) in dry acetonitrile (125 ml.) was treated with a 60% dispersion of sodium hydride in oil (1g, 25mM) 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, 150g) using 2% methanol in chloroform as eluant. Evaporation of the appropriate fractions followed by recrystallisation from hexane gave the title compound (1.9g, 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, 150g)
  4. customEvaporation of the appropriate fractions
  5. customfollowed by recrystallisation from hexane

Sources & evidence

ORD record
ord-09876656fdf047e18efced64b4e71d5e
Source dataset
uspto-grants-1980_01
Patent number
US04183854

Reaction notes

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