Imidazole → N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide

HRID 1078394Notes

Reaction equation

HRID 1078394 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[NH:16]1[CH:20]=[CH:19][N:18]=[CH:17]1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:11][C:12](=[O:15])[CH2:13][CH2:14][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 18349731N-[1-(4-chlorophenyl)-1-methylethyl]-acrylamide

Product 1

HCID 19429499N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of N-[1-(4-chlorophenyl)-1-methylethyl]acrylamide (200 g), imidazole (60.9 g), Triton B (20 ml) and 1,4-dioxane (1600 ml) was stirred and boiled under reflux for 20 hours. The solvent was removed under reduced pressure and the residue dissolved in dichloromethane (2000 ml). The mixture was extracted with 2M hydrochloric acid. The combined aqueous extracts were basified with 2M sodium hydroxide solution and extracted with dichloromethane to give N-[1-(4-chlorophenyl)-1-methylethyl]-3-(imidazol-1-yl)propionamide, m.p. 154°-155° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane (2000 ml)
  4. extractionThe mixture was extracted with 2M hydrochloric acid
  5. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-0aabdcbbc38d466f976218d0fad2104f
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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