Methyl morpholine oxide → 2-(3,4-Diethoxyphenyl)-4-formylthiazole

HRID 2097553Notes

Reaction equation

HRID 2097553 reaction equation
C[N+]1([O-])CC[O:5]CC1.Cl[CH2:10][C:11]1[N:12]=[C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH3:24])=[C:18]([O:25][CH2:26][CH3:27])[CH:17]=2)[S:14][CH:15]=1>C(#N)C>[CH2:26]([O:25][C:18]1[CH:17]=[C:16]([C:13]2[S:14][CH:15]=[C:11]([CH:10]=[O:5])[N:12]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH2:23][CH3:24])[CH3:27]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 187072782-(3,4-Diethoxyphenyl)-4-chloromethylthiazole

Product 1

HCID 187072072-(3,4-Diethoxyphenyl)-4-formylthiazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-methylmorpholine-N-oxide (16.5 g, 141 mmol) was added to a solution (200 ml) of 4-chloromethyl-2-(3,4-diethoxyphenyl)thiazole (13.99 g, 47 mmol) in acetonitrile, 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 salt 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=1/2). The solvent was distilled off under reduced pressure, to thereby obtain 11.2 g (yield: 86%) of 2-(3,4-diethoxyphenyl)thiazole-4-carboxaldehyde as a yellow solid.

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 salt 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=1/2)
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-568b5c1fd45a44a7806aa9a5b2f2c82b
Source dataset
uspto-grants-2013_05
Patent number
US08450352B2

Reaction notes

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