Iodoethane → HCID 68706020, compound

HRID 2097565Notes

Reaction equation

HRID 2097565 reaction equation
[CH2:1](I)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:20]2[S:21][CH:22]=[C:23]([CH2:25][C:26](=[O:36])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=3)[N:24]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].[C:37](OCC)(=O)[CH3:38]>CN(C=O)C>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([C:20]2[S:21][CH:22]=[C:23]([CH2:25][C:26](=[O:36])[CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH2:37][CH3:38])=[C:30]([O:35][CH2:1][CH3:2])[CH:29]=3)[N:24]=2)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 68711506HCID 68711506, compound

Product 1

HCID 68706020HCID 68706020, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Ethyl iodide (0.48 ml, 6.0 mmol) and potassium carbonate (0.62 g, 4.5 mmol) were added at room temperature to a solution (7 ml) of 3-[2-(3,4-dimethoxyphenyl)thiazole-4-yl]-1-(3,4-dihydroxyphenyl)propanone (0.58 g, 1.5 mmol) in DMF, followed by stirring at 60° C. for 1 hour. After cooling to room temperature, ethyl acetate was added to the reaction mixture, the resulting mixture was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2). The solvent was distilled off under reduced pressure, and the residue was recrystallized from an ethyl acetate/n-hexane mixed solvent, to thereby obtain 290 mg (yield: 44%) of 3-[2-(3,4-dimethoxyphenyl)thiazole-4-yl]-1-(3,4-diethoxyphenyl)propanone as a white powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting mixture was filtered
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2)
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was recrystallized from an ethyl acetate/n-hexane mixed solvent

Sources & evidence

ORD record
ord-339269bcce61470b83c3909fd028fbe0
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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