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

HRID 1698573노트

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HRID 1698573 반응식
[CH:1]([O:4][C:5](=[O:23])[CH2:6][N:7]1[C:11]2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=2[NH:9][C:8]1=O)([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:26])=O>>[CH:1]([O:4][C:5](=[O:23])[CH2:6][N:7]1[C:11]2[C:12]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[CH:13][CH:14]=[C:15]([Cl:16])[C:10]=2[N:9]=[C:8]1[Cl:26])([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 86632856Isopropyl [4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate

생성물 1

HCID 86632857Isopropyl [2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]acetate수율 97.2%

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온도
100 °C

실험 절차

A mixture of isopropyl[4-chloro-7-(1-ethylpropyl)-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl]acetate (3.73 g, 11.0 mmol) and phosphorus oxychloride (20 mL) was stirred at 100° C. for 48 hours. After cooling, phosphorus oxychloride was evaporated in vacuo. The residue was neutralized with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 5-15% ethyl acetate/hexane gradient mixture to give 3.82 g (10.7 mmol, 97.2%) of the title compound as an oil.

후처리

  1. temperatureAfter cooling
  2. customphosphorus oxychloride was evaporated in vacuo
  3. extractionextracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 5-15% ethyl acetate/hexane gradient mixture

출처 및 근거

ORD 기록
ord-73701df0537a43ceb970a029086bc07a
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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