1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 178440796, compound

HRID 1067667Notes

Reaction equation

HRID 1067667 reaction equation
[Br-].[C:2]1([CH2:8][CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:37]2[CH:41]=[C:40](C=O)[N:39]=[CH:38]2)C=CC=CC=1.[K].[C:57]([O-])(C)(C)C>C1COCC1>[NH:37]1[CH:41]=[C:40]([CH:9]([CH2:8][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH2:57])[N:39]=[CH:38]1

Participants

6

Reactant 4

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 45749132-Methylpropan-2-olateHCID 5462222PotassiumHCID 109286473-Phenylpropyl triphenylphosphonium bromide

Product 1

HCID 178440796HCID 178440796, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 mmol of 3-phenylpropyltriphenylphosphonium bromide, 10 mmol of (1-triphenylmethyl-1H-imidazol-4-yl)methanal (J. L. Kelley, C. A. Miller, E. W. Mc Lean, J. Med. Chem. 1977, 20, 721) and 12 mmol of potassium of t-butanolate are stirred for 24 hours in 50 ml THF. The solvent is evaporated off under reduced pressure, hydrolysed with water and extracted using chloroform. The concentrated organic extract is heated from reflux in 30 ml 2N HCl and 30 ml of acetone for 1 hour. The solvent is evaporated off under reduced pressure and triphenylmethanol is extracted using diethyl ether. The aqueous phase is alkalized using ammonia and the crude product is extracted using diethyl ether. The aqueous phase is alkalized using diethyl ether and crystallized as hydrogen maleate from diethyl ether and ethanol.

Workup

  1. customThe solvent is evaporated off under reduced pressure, hydrolysed with water
  2. extractionextracted
  3. extractionThe concentrated organic extract
  4. temperatureis heated
  5. temperaturefrom reflux in 30 ml 2N HCl
  6. customThe solvent is evaporated off under reduced pressure and triphenylmethanol
  7. extractionis extracted
  8. extractionthe crude product is extracted
  9. customcrystallized as hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-a4c6ae19dac64578b2008e550852aea2
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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