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

HRID 51299

Reaction equation

HRID 51299 reaction equation
[C:1](Cl)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:21]1[CH:25]=[C:24]([CH:26]=[O:27])[N:23]=[CH:22]1.C(N(CC)CC)C.O>CN(C)C=O>[C:1]([N:21]1[CH:25]=[C:24]([CH:26]=[O:27])[N:23]=[CH:22]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 764281H-Imidazole-4-carbaldehyde

Product 1

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of trityl chloride (9.5 g, 34.3 mmol) in N,N-dimethylformamide (50 ml) was added dropwise to an ice-cooled solution of imidazole-4-carboxaldehyde (3 g, 31.2 mmol) and triethylamine (17 ml, 125 mmol) in N,N-dimethylformamide (30 ml) and the solution was stirred for 2 hours. The reaction was then allowed to warm to room temperature, and was stirred for a further 18 hours. Water (200 ml) was added, and the resulting pink solid was collected and dried, then dissolved in dichloromethane (200 ml). The resulting solution was washed with water (2×100 ml), dried (MgSO4) and evaporated under reduced pressure. The product was recrystallised from ethanol to afford the title compound as a solid, 7.8 g. 1H-NMR (CDCl3, 400 MHz) δ: 7.06 (m, 6H), 7.32 (m, 9H), 7.48 (s, 1H), 7.58 (s, 1H), 9.82 (s, 1H). Microanalysis found: C, 81.54; H, 5.37; N, 8.24. C23H18N2O requires C, 81.63; H, 5.36; N, 8.28%.

Workup

  1. stirringwas stirred for a further 18 hours
  2. customthe resulting pink solid was collected
  3. customdried
  4. dissolutiondissolved in dichloromethane (200 ml)
  5. washThe resulting solution was washed with water (2×100 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customThe product was recrystallised from ethanol

Sources & evidence

ORD record
ord-7e4a9f9166434d7ba8d06a2ed98ab35d
Source dataset
uspto-grants-2004_03
Patent number
US06713496B2

Linked notes

Loading…