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

HRID 1698585ノート

反応式

HRID 1698585 の反応式
[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]2[O:18][CH:19]=[CH:20][CH:21]=2)=[CH:8][CH:7]=1)[CH2:4][CH3:5])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][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]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:10]=2[N:14]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 672733997-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one

生成物 1

HCID 672726412-Chloro-7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1H-benzimidazole収率 52.2%

反応条件

温度
120 °C

実験手順

A mixture of 7-(1-ethylpropyl)-4-(2-furyl)-1-methyl-1,3-dihydro-2H-benzimidazole-2-one (79 mg, 0.278 mmol) in phosphorous oxychloride (0.78 ml, 8.33 mmol) was stirred at 120° C. for 2 h. The reaction was allowed to cool to room temperature and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with aqueous saturated sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture to give 44 mg (0.145 mmol, 52%) of the title compound.

後処理

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with aqueous saturated sodium bicarbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel with a 1-30% ethyl acetate/n-hexane gradient mixture

出典と根拠

ORDレコード
ord-ad01b4862c254ed391cb936db83979ab
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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