Trityl chloride → 1-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

HRID 865086Notes

Reaction equation

HRID 865086 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(N(CC)CC)C.[C:15]1([C:21](Cl)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[C:15]1([C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:1]2[CH:5]=[CH:4][N:3]=[C:2]2[CH:6]=[O:7])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 249551H-imidazole-2-carbaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehydeYield 90.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1.5 g of 2-imidazole carboxaldehyde was dissolved in 20 ml of dimethylformamide, 2.18 ml of triethylamine and 4.3 g of triphenylmethyl chloride were added to the above solution, and then the resulting mixture was stirred at room temperature for 24 hours. A saturated sodium bicarbonate aqueous solution and chloroform were added to the reaction solution, and the resulting organic layer was collected, washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate, followed by evaporation of the solvent. The residue was subjected to silica gel chromatography eluted with dichloromethane-methanol (50:1) to obtain 4.717 g of 1-triphenylmethyl-2-imidazole carboxaldehyde.

Workup

  1. customthe resulting organic layer was collected
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. customfollowed by evaporation of the solvent
  5. washeluted with dichloromethane-methanol (50:1)

Sources & evidence

ORD record
ord-1b3b2f2682394a8f9136632e93d4d9ac
Source dataset
uspto-grants-1996_10
Patent number
US05565479

Reaction notes

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