Phosphorus oxychloride → Ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate

HRID 1628391노트

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HRID 1628391 반응식
[Cl:1][C:2]1[C:10]2[NH:9][C:8](=O)[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]=2[C:5]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:8]1[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]2[C:5]([CH:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[N:9]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 86632859Ethyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

생성물 1

HCID 86632860Ethyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate수율 92%

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온도
90 °C

실험 절차

A mixture of ethyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate (2.57 g, 7.91 mmol) and phosphorus oxychloride (15 mL) was stirred at 90° C. for 3 days. After cooling, phosphorus oxychloride was evaporated in vacuo. The residue was poured into ice-cold 2N aqueous sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-20% ethyl acetate/n-hexane gradient mixture to give the title compound (2.49 g, 7.25 mmol, 92%) as an oil.

후처리

  1. temperatureAfter cooling
  2. customphosphorus oxychloride was evaporated in vacuo
  3. additionThe residue was poured into ice-cold 2N aqueous sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 10-20% ethyl acetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-613eeeb4e32645878c5b310845a54fd3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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