Imidazole → HCID 10353773, compound

HRID 329441Notes

Reaction equation

HRID 329441 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][C:10]([NH:12][C:13]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:20])=[O:11].O>CN(C)C=O>[CH3:19][C:18]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:20])[C:13]=1[NH:12][C:10](=[O:11])[CH2:9][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Product 1

HCID 10353773HCID 10353773, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.0 g of a 60% oil dispersion of sodium hydride in 90 ml of dimethylformamide was stirred and heated at 50° C. during the portionwise addition of 10.32 g of imidazole. After stirring for 20 minutes, 15.0 g of 2-chloro-N-(2,6-dimethylphenyl)acetamide was added and heating was continued for an additional 30 minutes. Water was added and the reaction mixture was evaporated to dryness. The residue was dissolved in 2N hydrochloric acid, washed with ether, made strongly basic with excess sodium hydroxide and the product was extracted with dichloromethane. The combined organic layers were dried with sodium sulfate and evaporated to give 14 g of N-(2,6-dimethylphenyl)-1H-imidazole-1-acetamide, mp 160°-162° C.

Workup

  1. stirringAfter stirring for 20 minutes
  2. temperatureheating
  3. customthe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in 2N hydrochloric acid
  5. washwashed with ether
  6. extractionthe product was extracted with dichloromethane
  7. dry with materialThe combined organic layers were dried with sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-f9b69234f9c54cb5ad9136a731036774
Source dataset
uspto-grants-1990_01
Patent number
US04891429

Reaction notes

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