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

HRID 1698606노트

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HRID 1698606 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]([F:20])([F:19])[F:18])=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:23])=O>>[Cl:23][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]([F:20])([F:19])[F:18])[C:10]=2[N:14]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 672729847-(1-Ethylpropyl)-1-methyl-4-(trifluoromethyl)-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 672728702-Chloro-7-(1-ethylpropyl)-1-methyl-4-(trifluoromethyl)-1H-benzimidazole수율 91%

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온도
110 °C

실험 절차

A mixture of 7-(1-ethylpropyl)-1-methyl-4-(trifluoro-methyl)-1,3-dihydro-2H-benzimidazol-2-one (310 mg, 1.08 mmol) and phosphoryl chloride (5 ml) was heated at 110° C. for 1 h and concentrated in vacuo. Toluene was added and concentrated again to remove excess reagent. Aqueous saturated sodium bicarbonate was added to the residue and extracted with ethyl acetate. The extracts were washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel with a 20% ethyl acetate/n-hexane to give 300 mg (0.99 mmol, 91%) of the title compound as a colorless oil.

후처리

  1. concentrationconcentrated in vacuo
  2. additionToluene was added
  3. concentrationconcentrated again
  4. customto remove excess reagent
  5. additionAqueous saturated sodium bicarbonate was added to the residue
  6. extractionextracted with ethyl acetate
  7. washThe extracts were washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography on silica gel with a 20% ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-362cf988a8ee47c09f5151899e145138
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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