Imidazole → HCID 18349742, compound

HRID 378600Notes

Reaction equation

HRID 378600 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][C:8]([NH:11][C:12](=[O:15])[CH:13]=[CH2:14])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.O1CCOCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:11][C:12](=[O:15])[CH2:13][CH2:14][N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)([CH3:9])[CH3:10])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 312751,4-DioxaneHCID 66854Benzyltrimethylammonium hydroxideHCID 18349804HCID 18349804, compound

Product 1

HCID 18349742HCID 18349742, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of N-[2-(4-chlorophenoxy)-1,1-dimethylethyl]acrylamide (4.5 g), imidazole (1.24 g), benzyltrimethylammonium hydroxide (0.62 ml of a 40% solution in methanol, Triton®B) and 1,4-dioxane (40 ml) was heated at 95° C. for 7 hours. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane. This solution was extracted with 5M hydrochloric acid. The combined acid extracts were basified with 10M sodium hydroxide solution and extracted with dichloromethane to give N-[2-(4-chlorophenoxy)-1,1-dimethylethyl]-3-(imidazol-1-yl)propionamide.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. extractionThis solution was extracted with 5M hydrochloric acid
  4. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-f8acc73ffc7a46d181fe4ca574808094
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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