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

HRID 1698573ノート

反応式

HRID 1698573 の反応式
[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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-73701df0537a43ceb970a029086bc07a
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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