Trityl chloride → 1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

HRID 1929384Notes

Reaction equation

HRID 1929384 reaction equation
C(N(CC)CC)C.[NH:8]1[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9]1.[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>CN(C)C=O>[C:21]([N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[N:10]=[CH:9]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (3.05 ml, 21.86 mmol) was added to a solution of 1H-imidazole-4-carbaldehyde (2 g, 20.82 mmol) and triphenylmethyl chloride (5.80 g, 20.82 mmol) in N,N-dimethylformamide (20 ml). The reaction mixture was stirred at room temperature for 18 hours. The crude mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The organic phase was washed dried over sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallised from dichloromethane and hexanes to afford the title compound as a cream solid (4.7 g, 67% yield).

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallised from dichloromethane and hexanes

Sources & evidence

ORD record
ord-88478c7463d04d828404437fd45b0609
Source dataset
uspto-grants-2012_05
Patent number
US08188071B2

Reaction notes

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