Hydrogen Peroxide → 5-Thiazolecarboxylic acid, 4-methyl-, ethyl ester

HRID 550536Notes

Reaction equation

HRID 550536 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=S)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].OO.C([O-])(O)=O.[Na+]>Cl>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 3957801Ethyl 4-methyl-2-sulfanyl-1,3-thiazole-5-carboxylate

Product 1

HCID 2986105-Thiazolecarboxylic acid, 4-methyl-, ethyl esterYield 23.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 4-methyl-2-thioxo-2,3-dihydro-1,3-thiazole-5-carboxylate (2.51 g) in HCl (37%, 8 mL) was warmed to 50° C., H2O2 (30%, 4.2 g) was added dropwise over 20 min and the reaction mixture was stirred for 1 h and allowed to reach room temperature. The mixture was then treated with NaHCO3 up to a slightly basic pH and extracted twice with ether (2×20 mL), the organic phase separated and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica gel (eluting with cyclohexane : ethyl acetate from 1:0 to 7:3) to give the title compound (0.5 g). MS (m/z): 172 [MH]+.

Workup

  1. customto reach room temperature
  2. extractionextracted twice with ether (2×20 mL)
  3. customthe organic phase separated
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was purified by flash chromatography on silica gel (eluting with cyclohexane : ethyl acetate from 1:0 to 7:3)

Sources & evidence

ORD record
ord-636427c892244029a2b18a4634f78d3b
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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