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

HRID 1441704노트

반응식

HRID 1441704 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f0831d0a383e42f39e524a7858e8b8f6
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07655680B2

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