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

HRID 401495Notes

Reaction equation

HRID 401495 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-17f731ac6baf44c580e08c51e88315b6
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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