1,3-Dichloroacetone → 2-(3,4-Diethoxyphenyl)-4-chloromethylthiazole

HRID 2097552Notes

Reaction equation

HRID 2097552 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].[Cl:16][CH2:17][C:18]([CH2:20]Cl)=O>C(O)C>[Cl:16][CH2:17][C:18]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH3:15])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=2)[S:8][CH:20]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 77452503,4-Diethoxybenzene-1-carbothioamide

Product 1

HCID 187072782-(3,4-Diethoxyphenyl)-4-chloromethylthiazoleYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,4-diethoxythiobenzamide (30.0 g, 133 mmol) was suspended in ethanol (300 ml), and 1,3-dichloroacetone (12.8 ml, 135 mmol) was added, followed by heating under reflux for 4 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 dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3). The solvent was distilled off under reduced pressure, and the residue was recrystallized from an ethyl acetate/n-hexane mixed solvent, to thereby obtain 26.9 g (yield: 68%) of 4-chloromethyl-2-(3,4-diethoxyphenyl)thiazole as yellow prisms.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 4 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 materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3)
  9. distillationThe solvent was distilled off under reduced pressure
  10. customthe residue was recrystallized from an ethyl acetate/n-hexane mixed solvent

Sources & evidence

ORD record
ord-9c07c236d97c478aac59d40bf829b84c
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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