Water → 1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

HRID 922712Notes

Reaction equation

HRID 922712 reaction equation
[CH3:1][C:2]([N:4]([CH3:6])C)=O.C([N:9]([CH2:12]C)CC)C.[C:14](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH2:34]>CO>[C:14]([N:9]1[CH:12]=[C:2]([CH:1]=[O:34])[N:4]=[CH:6]1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 31374Dimethylacetamide

Product 1

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4(5)-formylimidazole (2 g, 20.8 mmol) were added DMAc (30 mL) and triethylamine (3.5 mL, 25.0 mmol, 1.2 equivalents), and then trityl chloride (4.06 g, 14.6 mmol, 0.7 equivalents) was added thereto at room temperature. The mixture was stirred at room temperature for 24 hr, and to the reaction mixture was added water (60 mL) at room temperature, and the mixture was stirred at room temperature for 2 hr. The crystals were collected by filtration, washed with water, and vacuum-dried (50° C.) to a constant amount to give a crude compound (4.6 g). To the crude compound (0.2 g) was added methanol (1 mL), and the mixture was stirred at room temperature for 2 hr. The crystals were collected by filtration, was washed with methanol (0.2 mL), and vacuum-dried (50° C.) to a constant amount to give 1-trityl-4-formyl-1H-imidazole (0.14 g). yield 65%.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature for 2 hr
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water
  5. customvacuum-dried (50° C.) to a constant amount
  6. customto give a crude compound (4.6 g)
  7. stirringthe mixture was stirred at room temperature for 2 hr
  8. filtrationThe crystals were collected by filtration
  9. washwas washed with methanol (0.2 mL)
  10. customvacuum-dried (50° C.) to a constant amount

Sources & evidence

ORD record
ord-6e744e94663348d1ac24756ee1def480
Source dataset
uspto-grants-2016_03
Patent number
US09278938B2

Reaction notes

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