Phosphorus oxychloride → 2-Chloro-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazole

HRID 1698551노트

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HRID 1698551 반응식
[CH3:1][C:2]1[N:3]([C:8]2[C:13]3[N:14]([CH3:18])[C:15](=O)[NH:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:15]1[N:14]([CH3:18])[C:13]2[C:8]([N:3]3[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]3[CH3:7])=[CH:9][CH:10]=[CH:11][C:12]=2[N:16]=1

참가 물질

3

반응물 2

HCID 24813Phosphorus oxychlorideHCID 672731377-(2,5-Dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one

생성물 1

HCID 672730232-Chloro-7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-benzimidazole수율 72%

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온도
85 °C

실험 절차

A mixture of 239 mg (0.991 mmol) of 7-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one in 2 mL of phosphorus oxychloride was stirred at 85° C. for 4 hours. After cooling, phosphorus oxychloride was evaporated in vacuo. The residue was diluted with ice and neutralized by aqueous sodium hydroxide. The aqueous suspension was extracted with ethyl acetate (X2). The combined organic layer was washed with water (X1) and brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 10-20% ethylacetate/n-hexane gradient mixture to give 185 mg (72%) of the title compound.

후처리

  1. temperatureAfter cooling
  2. customphosphorus oxychloride was evaporated in vacuo
  3. additionThe residue was diluted with ice
  4. extractionThe aqueous suspension was extracted with ethyl acetate (X2)
  5. washThe combined organic layer was washed with water (X1) and brine (X1)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a 10-20% ethylacetate/n-hexane gradient mixture

출처 및 근거

ORD 기록
ord-316de8c685814b708e15e3fab06ce74c
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163935B2

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