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

HRID 2291869Notes

Reaction equation

HRID 2291869 reaction equation
[OH:1][C:2]1[CH:20]=[CH:19][C:5]([NH:6][C:7](=[O:18])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][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:13]1([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]([NH:6][C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([CH3:38])([CH3:39])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:20][CH:19]=2)=[O:18])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10444833Ethyl 6-bromo-2,2-dimethylhexanoateHCID 13422031p-Hydroxy-6-(1-imidazolyl)hexaneanilide

Product 1

HCID 13422043Ethyl 6-[p-[6-(1-imidazolyl)hexanamido]phenoxy]-2,2-dimethylhexanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 20 ml of ethanol were added 1.37 g of p-hydroxy-6-(1-imidazolyl)hexaneanilide and 0.69 g of anhydrous potassium carbonate and the mixture was stirred for 30 minutes with heating under reflux. After cooling, 1.26 g of ethyl 6-bromo-2,2-dimethylhexanoate was added thereto and the mixture was reacted overnight with heating under reflux. The solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the resulting residue followed by extracting with chloroform. After the chloroform layer was successively washed with a 1N aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure and the resulting residue was subjected to silica gel column chromatography. The product was eluted out using a chloroform-methanol liquid mixture (50:1 in a volume ratio). The solvent was removed by distillation under reduced pressure. The resulting crystals were recrystallized from a solvent mixture of n-hexane-ethyl acetate to obtain ethyl 6-[p-[6-(1-imidazolyl)hexanamido]phenoxy]-2,2-dimethylhexanoate as white crystals.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe mixture was reacted overnight
  5. temperaturewith heating
  6. temperatureunder reflux
  7. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  8. additionWater was added to the resulting residue
  9. extractionby extracting with chloroform
  10. washAfter the chloroform layer was successively washed with a 1N aqueous sodium hydroxide solution
  11. dry with materiala saturated aqueous sodium chloride solution, it was dried over anhydrous magnesium sulfate
  12. customThe solvent was removed by distillation under reduced pressure
  13. washThe product was eluted out
  14. customThe solvent was removed by distillation under reduced pressure
  15. customThe resulting crystals were recrystallized from a solvent mixture of n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-df96672a18da49dcb11c56c43c334b87
Source dataset
uspto-grants-1989_01
Patent number
US04798838

Reaction notes

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