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

HRID 1698551ノート

反応式

HRID 1698551 の反応式
[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

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-316de8c685814b708e15e3fab06ce74c
出典データセット
uspto-grants-2012_04
特許番号
US08163935B2

反応ノート

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