Phosphorus oxychloride → 2-Chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole

HRID 1698585노트

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HRID 1698585 반응식
[CH2:1]([CH:3]([C:6]1[C:11]2[N:12]([CH3:16])[C:13](=O)[NH:14][C:10]=2[C:9]([C:17]2[O:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:13]1[N:12]([CH3:16])[C:11]2[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:7][CH:8]=[C:9]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:10]=2[N:14]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 672733997-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one

생성물 1

HCID 672726412-Chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole수율 52.2%

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온도
120 °C

실험 절차

A mixture of 7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one (79 mg, 0.278 mmol) in phosphorous oxychloride (0.78 ml, 8.33 mmol) was stirred at 120° C. for 2 h. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture to give 44 mg (0.145 mmol, 52%) of the title compound.

후처리

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-ad01b4862c254ed391cb936db83979ab
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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