Cesium carbonate → Tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

HRID 1643931ノート

反応式

HRID 1643931 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.Br[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:24]([O:23][C:21]([CH2:20][N:8]1[C:4]2[CH:3]=[C:2]([Cl:1])[CH:18]=[CH:17][C:5]=2[N:6]([C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[C:7]1=[O:9])=[O:22])([CH3:27])([CH3:26])[CH3:25]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 10468275tert-Butyl 5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

生成物 1

HCID 66754580Tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4.00 g (14.9 mmol) of tert-butyl 5-chloro-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate (Via), 3.19 g (16.4 mmol) of tert-butyl bromoacetate and 7.28 g (22.3 mmol) of cesium carbonate in acetonitrile (80 ml) was heated under reflux for 3 h. The solvent was removed in vacuo, the residue was mixed with water, and the aqueous mixture was extracted four times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by chromatography on silica gel (mobile phase gradient 0-5% ethyl acetate in dichloromethane).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. additionthe residue was mixed with water
  5. extractionthe aqueous mixture was extracted four times with ethyl acetate
  6. washThe combined organic phases were washed with saturated NaCl solution
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified by chromatography on silica gel (mobile phase gradient 0-5% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-897966094cb44adaa3c9c01ce8574735
出典データセット
uspto-grants-2012_02
特許番号
US08119676B2

反応ノート

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