Sodium hydride → Ethyl 6-chloro-3-(ethoxycarbonylphenylmethyl)-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

HRID 1631965ノート

反応式

HRID 1631965 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:9][C:8](=[O:10])[N:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:16]=1.[H-].[Na+].Br[CH:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22].[Cl-].[NH4+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([CH:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:8](=[O:10])[N:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:16]=1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 97780Ethyl bromophenylacetateHCID 10354291Ethyl 6-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

生成物 1

HCID 24901020Ethyl 6-chloro-3-(ethoxycarbonylphenylmethyl)-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

1.38 g (5.73 mmol) of ethyl 6-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (Va) were dissolved in dry DMF (20 ml) in a heat-dried flask under a nitrogen atmosphere. 240 mg (6.02 mmol) of sodium hydride (60% suspension in mineral oil) were added while stirring at 0° C., and the reaction solution was then stirred at room temperature for 30 min. After renewed cooling in an ice bath, 1.53 g (6.31 mmol) of ethyl bromo-phenylacetate were added, and the mixture was stirred while cooling in ice for 1 h and then at room temperature for 2 h. The reaction solution was diluted with ethyl acetate, mixed with 10% aqueous ammonium chloride solution and then extracted with ethyl acetate (4×). The combined organic phases were washed with water and saturated NaCl solution, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane). Yield: 2.03 g (88%) of colorless oil

後処理

  1. stirringthe reaction solution was then stirred at room temperature for 30 min
  2. temperatureAfter renewed cooling in an ice bath
  3. stirringthe mixture was stirred
  4. temperaturewhile cooling in ice for 1 h
  5. extractionextracted with ethyl acetate (4×)
  6. washThe combined organic phases were washed with water and saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by chromatography on silica gel (mobile phase 50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-2fa34b619ef94191828dab4cbaf2b905
出典データセット
uspto-grants-2014_07
特許番号
US08791148B2

反応ノート

読み込み中…