Acetic Acid → HCID 15099411, compound

HRID 1706378Notes

Reaction equation

HRID 1706378 reaction equation
[CH2:1]([N:8]1[C:12](CC#N)=[C:11]([Cl:16])[N:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:27]([OH:30])(=[O:29])[CH3:28]>Cl>[CH2:1]([N:8]1[C:12]([CH2:28][C:27]([OH:30])=[O:29])=[C:11]([Cl:16])[N:10]=[C:9]1[C:17]1[CH:18]=[CH:19][C:20]([N:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 13022619HCID 13022619, compound

Product 1

HCID 15099411HCID 15099411, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5 g of 1-benzyl-2-(p-dimethylaminophenyl)-4-chloro-5-cyanomethylimidazole was refluxed in a mixture of 25 ml concentrated hydrochloric acid, 25 ml water and 25 ml glacial acetic acid for 3 hours. The reaction mixture was concentrated to dryness under reduced pressure, the residue dissolved in 50 ml of water and the solution adjusted to pH 3 with sodium hydrogen carbonate. The resulting precipitate was recovered by filtration and recrystallized from aqueous ethanol. By the above procedure was obtained 4 g of 1-benzyl-2-(p-dimethylaminophenyl)-4-chloroimidazole-5-acetic acid as pale yellow needles, m.p. 170°-180° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. dissolutionthe residue dissolved in 50 ml of water
  3. filtrationThe resulting precipitate was recovered by filtration
  4. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-8c8448c6503149e98af13073fb1f1393
Source dataset
uspto-grants-1980_06
Patent number
US04207324

Reaction notes

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