3,4-Diethoxybenzene-1-carbothioamide → HCID 68711915, compound

HRID 1441708Notes

Reaction equation

HRID 1441708 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([NH2:9])=[S:8])[CH3:2].[C:16]([CH:24]([CH2:30][C:31](=O)[CH2:32]Br)[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[S:8][CH:32]=[C:31]([CH2:30][CH:24]([C:16](=[O:23])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:9]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]

Participants

4

Reactant 2

HCID 77452503,4-Diethoxybenzene-1-carbothioamideHCID 86618358HCID 86618358, compound

Product 1

HCID 68711915HCID 68711915, compoundYield 112.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-diethoxythiobenzamide (0.63 g, 2.8 mmol) was added to a solution (20 ml) of ethyl 2-benzoyl-5-bromo-4-oxopentanoate (0.90 g, 2.8 mmol) in ethanol, followed by heating under reflux for 1.5 hours. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the residue was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated salt solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, to thereby obtain 1.43 g (yield: 65%) of ethyl 2-[2-(3,4-diethoxyphenyl)thiazole-4-ylmethyl]-3-oxo-3-phenylpropionate as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionthe residue was subjected to extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  6. dry with materiala saturated salt solution, and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-89312107e36d4804a7991b105df744c6
Source dataset
uspto-grants-2010_02
Patent number
US07655680B2

Reaction notes

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