Imidazole → HCID 18349742, compound

HRID 2268230Notes

Reaction equation

HRID 2268230 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-].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 961HydroxideHCID 312751,4-DioxaneHCID 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)-1,1dimethylethyl]acrylamide (4.5 g), imidazole (1.24 g), benzyltrimethylanmonium 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 SM 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 SM hydrochloric acid
  4. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-10a988deced14b37bc88d3b10fcdf43b
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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