Sodium Bicarbonate → Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 1904294Notes

Reaction equation

HRID 1904294 reaction equation
Cl[CH:2]([C:8]([C:10]([F:13])([F:12])[F:11])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14]([NH2:17])(=[S:16])[CH3:15].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:15][C:14]1[S:16][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]([F:13])([F:12])[F:11])[N:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723949ThioacetamideHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 1486077Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylateYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6.00 g of ethyl 2-chloro-4,4,4-trifluoroacetoacetate and 2.06 g of thioacetamide were dissolved in 30 ml of acetic acid and the mixture was refluxed for 6 hours with stirring. The resulting solution was neutralized with aqueous sodium bicarbonate solution, then extracted with ethyl acetate and the organic layer was concentrated. The residue was chromatographed on silica gel (eluent; n-hexane:chloroform:tetrahydrofuran=6:2:1 V/V) to obtain 3.7 g of ethyl 2-methyl-4-trifluoromethylthiazole-5-carboxylate (yield 56%).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. extractionextracted with ethyl acetate
  3. concentrationthe organic layer was concentrated
  4. customThe residue was chromatographed on silica gel (eluent; n-hexane:chloroform:tetrahydrofuran=6:2:1 V/V)

Sources & evidence

ORD record
ord-3e9e37eac90f4cc69ed860e8e3fb9954
Source dataset
uspto-grants-1989_06
Patent number
US04837242

Reaction notes

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