15-Crown-5 → HCID 178447070, compound

HRID 1067663

Reaction equation

HRID 1067663 reaction equation
C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O-:16])[N:10]=[CH:9]2)C=CC=CC=1.[Na+].[Br-].[CH3:31][CH:32]([CH3:35])[CH2:33][CH3:34].O1CCOCCOCCOCCOCC1>C1(C)C=CC=CC=1>[CH3:31][CH:32]([CH3:35])[CH2:33][CH2:34][O:16][CH2:15][CH2:14][CH2:13][C:11]1[N:10]=[CH:9][NH:8][CH:12]=1

Participants

5

Reactant 3

HCID 3633615-Crown-5HCID 211936043-Methylbutane bromideHCID 23682245sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate

Product 1

HCID 178447070HCID 178447070, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

5 mmol of sodium 3-(1-triphenylmethyl-1H-imidazol-4-yl)propanolate, 5 mmol of 3-methylbutane bromide and 0.5 mmol of 15-crown-15 (1, 4, 7, 10, 13-pentaoxacyclopentadecane) dissolved in 10 ml of anhydrous toluene are refluxed for 24 hours. The solvent is then evaporated off, and the residue dissolved in 10 ml THF and 30 ml 2N HCl and then heated at 70° C. for 2 hours. The THF is evaporated off under reduced pressure and triphenylmethanol is extracted with diethyl ether. The aqueous phase is neutralized with potassium carbonate and the product is extracted with diethyl ether. The organic extract is dried and evaporated, giving rise to an oil, which is crystallized as hydrogen maleate from diethyl ether and ethanol.

Workup

  1. temperatureare refluxed for 24 hours
  2. customThe solvent is then evaporated off
  3. dissolutionthe residue dissolved in 10 ml THF
  4. customThe THF is evaporated off under reduced pressure and triphenylmethanol
  5. extractionis extracted with diethyl ether
  6. extractionthe product is extracted with diethyl ether
  7. extractionThe organic extract
  8. customis dried
  9. customevaporated
  10. customgiving rise to an oil, which
  11. customis crystallized as hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-591bdee9a8134fd883b97e6fd5bd97c6
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Linked notes

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