4-Methoxybenzenecarbothioamide → Ethyl 2-(4-methoxyphenyl)-5-thiazoleacetate

HRID 2076640Notes

Reaction equation

HRID 2076640 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.Br[CH:13]([CH:20]=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>ClCCCl.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]2[S:8][C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 7368274-MethoxybenzenecarbothioamideHCID 15576269Ethyl 3-bromo-4-oxobutanoate

Product 1

HCID 25247878Ethyl 2-(4-methoxyphenyl)-5-thiazoleacetateYield 67%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methoxythiobenzamide (1.62 g, 9.7 mmol) and ethyl 3-bromo-4-oxobutanoate (2.02 g, 9.7 mmol) were suspended in 1,2-dichloroethane (25 ml), and the mixture was heated under reflux for 3 hours. The reaction mixture was diluted with ethyl acetate, successively washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give ethyl [2-(4-methoxyphenyl)-1,3-thiazol-5-yl]acetate (1.79 g, yield: 67%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washsuccessively washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-21e17e0fa7a44baea3ece210f742a9a8
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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