Dimethylamine → 3-(Trifluoromethyl)phenyl-5-(dimethylamino)-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde

HRID 67245Notes

Reaction equation

HRID 67245 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([N:9]2[C:13](Cl)=[C:12]([CH:15]=[O:16])[N:11]([CH3:17])[C:10]2=[O:18])[CH:6]=[CH:7][CH:8]=1.[CH3:21][NH:22][CH3:23]>>[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([N:9]2[C:13]([N:22]([CH3:23])[CH3:21])=[C:12]([CH:15]=[O:16])[N:11]([CH3:17])[C:10]2=[O:18])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 130655131-(3-(trifluoromethyl)phenyl)-5-chloro-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde

Product 1

HCID 130655143-(Trifluoromethyl)phenyl-5-(dimethylamino)-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde

Procedure

A solution of 750 mg. of 1-(3-(trifluoromethyl)phenyl)-5-chloro-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde from Example 14 and 15 ml. of 25% aqueous dimethylamine was warmed on a steam bath for 5 minutes. The solution was cooled and the solid was collected by filtration and recrystallized from ethanol-water. After drying the product at 50° C. for 30 minutes, 320 mg. of 1-(3-(trifluoromethyl)phenyl)-5-chloro-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde was recovered. M.P. 87°-90° C.

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe solid was collected by filtration
  3. customrecrystallized from ethanol-water
  4. customAfter drying the product at 50° C. for 30 minutes
  5. customof 1-(3-(trifluoromethyl)phenyl)-5-chloro-2,3-dihydro-3-methyl-2-oxo-1H-imidazole-4-carboxaldehyde was recovered

Sources & evidence

ORD record
ord-1b08e1b78c304f03baf10d63f2275122
Source dataset
uspto-grants-1982_08
Patent number
US04345936

Reaction notes

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