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

HRID 2097557Notes

Reaction equation

HRID 2097557 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-715a81a7b219420799e4b3c257a507f9
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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