Potassium Carbonate → Ethyl 5-[p-[6-(1-imidazolyl)hexanamido]phenoxy]-2,2-dimethylpentanoate

HRID 2291865Notes

Reaction equation

HRID 2291865 reaction equation
Cl.[OH:2][C:3]1[CH:21]=[CH:20][C:6]([NH:7][C:8](=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH2:31][C:32]([CH3:39])([CH3:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(O)C>[N:14]1([CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([NH:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH2:29][CH2:30][CH2:31][C:32]([CH3:38])([CH3:39])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:21][CH:20]=2)=[O:19])[CH:18]=[CH:17][N:16]=[CH:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoateHCID 134220324'-Hydroxy-6-(1-imidazolyl)hexaneanilide hydrochloride

Product 1

HCID 13422034Ethyl 5-[p-[6-(1-imidazolyl)hexanamido]phenoxy]-2,2-dimethylpentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was suspended 3 g of 4'-hydroxy-6-(1-imidazolyl)hexaneanilide hydrochloride. While stirring 2.8 g of anhydrous potassium carbonate and 2.4 g of ethyl 5-bromo-2,2-dimethylpentanoate were added to the suspension. The mixture was stirred for 8 hours under reflux. The solvent was removed from the reaction mixture by distillation under reduced pressure and the residue was dissolved in ethylene chloride. The solution was successively washed with a 5% aqueous hydrogen sodium carbonate solution, water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. After drying, the solvent was removed by distillation under reduced pressure. The resulting crystals were recrystallized from ethyl acetate to give the aimed product, ethyl 5-[p-[6-(1-imidazolyl)hexanamido]phenoxy]-2,2-dimethylpentanoate.

Workup

  1. additionwere added to the suspension
  2. temperatureunder reflux
  3. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  4. dissolutionthe residue was dissolved in ethylene chloride
  5. washThe solution was successively washed with a 5% aqueous hydrogen sodium carbonate solution, water
  6. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  7. customAfter drying
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2b8c8866f7ef43c7b5a9e895dbb0a6c2
Source dataset
uspto-grants-1989_01
Patent number
US04798838

Reaction notes

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