Ethanol → HCID 86749503, compound

HRID 440597Notes

Reaction equation

HRID 440597 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].Br[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29]C(OCC)=O.O.O.O.[C:38]([O-:41])(=[O:40])C.[Na+].[CH2:43](O)[CH3:44]>>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]([C:38]([O:41][CH2:43][CH3:44])=[O:40])[CH2:29][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:23]=3)=[CH:15][CH:16]=2)[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 4

HCID 702EthanolHCID 2780092Ethyl 2-(2-bromophenyl)acetateHCID 23665404Sodium Acetate TrihydrateHCID 54524981HCID 54524981, compound

Product 1

HCID 86749503HCID 86749503, compound

Procedure

1.0 g (3.6 mMol) of 2-n-butyl-1-[(4-amino)benzyl]-benzimidazole, 0.87 g (3.6 mMol) of ethyl 2-bromo-phenylacetate and 0.5 g of sodium acetate-trihydrate are dissolved in 20 ml of ethanol and stirred for 18 hours at ambient temperature. Then the reaction mixture is refluxed for a further 4 hours. The solvent is evaporated down, water is added to the residue which is made alkaline with dilute ammonia solution and extracted with ethyl acetate. The combined organic phases are washed with water, dried over magnesium sulphate and concentrated by evaporation. The residue is purified over a silica gel column (particle size: 0.063-0.02 mm), using petroleum ether with 10-15% ethyl acetate as eluant. The uniform fractions are combined and evaporated down.

Workup

  1. temperatureThen the reaction mixture is refluxed for a further 4 hours
  2. customThe solvent is evaporated down
  3. additionwater is added to the residue which
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases are washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated by evaporation
  8. customThe residue is purified over a silica gel column (particle size: 0.063-0.02 mm)
  9. customevaporated down

Sources & evidence

ORD record
ord-c9dd93cd950241ba937cc8162457cf90
Source dataset
uspto-grants-1996_05
Patent number
US05519138

Reaction notes

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