Water → HCID 18782914, compound

HRID 1420779Notes

Reaction equation

HRID 1420779 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[CH:13]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[C:34](=[O:36])[CH3:35].[OH-].[Na+].O>C(O)C>[O:36]=[C:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[NH2:27])/[CH:35]=[CH:13]/[C:9]1[N:8]([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 110862'-AminoacetophenoneHCID 14798Sodium HydroxideHCID 6182531-(triphenylmethyl)-1H-imidazole-2-carbaldehyde

Product 1

HCID 18782914HCID 18782914, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Triphenylmethyl-2-imidazole carbaldehyde (4) (25.0 g, 74 mmol) and 2'-aminoacetophenone (10.0 g, 74 mmol) were suspended in 700 ml of ethanol, and a 25% aqueous solution (120 ml) of sodium hydroxide was added to the suspension, The mixture was stirred at room temperature for 12 hours. Water (3,000 ml) was added to the resultant reaction mixture, and crystals deposited were collected by filtration, washed with water and dried. The thus-obtained crystals were recrystallized from ethanol to obtain 17.6 g (yield: 52%) of 2-[(E)-3-oxo-3-(2-aminophenyl)-1-propenyl]-1-triphenylmethylimidazole.

Workup

  1. customreaction mixture, and crystals
  2. filtrationdeposited were collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe thus-obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-99dd1796f1a249d3899e96a73e46f180
Source dataset
uspto-grants-2000_06
Patent number
US06071943

Reaction notes

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