Water → HCID 178424858, compound

HRID 325946

Reaction equation

HRID 325946 reaction equation
Cl.Cl[CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1.CN(C)C=O.O.[C:15]1([CH3:23])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1>>[CH3:23][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[CH2:3][C:4]1[N:5]=[CH:6][NH:7][CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 7947MesityleneHCID 178478565HCID 178478565, compound

Product 1

HCID 178424858HCID 178424858, compound

Procedure

3.0 g of 4-chloromethylimidazole hydrochloride are suspended in 20 ml of mesitylene. 5 ml of dimethylformamide are added and the reaction mixture is refluxed for 12 hours, then cooled. 30 ml of water are added, the layers are separated, and the aqueous phase is washed with chloroform. The aqueous solution is then made alkaline with sodium carbonate solution and extracted with chloroform. The combined chloroform extracts are washed with water and evaporated to dryness. The residue, which is crude 4-(2',4',6'-trimethylbenzyl)imidazole, is converted to the hydrochloride by treatment with concentrated hydrochloric acid. The hydrochloride salt melts at 166°-169° C.

Workup

  1. temperaturethe reaction mixture is refluxed for 12 hours
  2. temperaturecooled
  3. customthe layers are separated
  4. washthe aqueous phase is washed with chloroform
  5. extractionextracted with chloroform
  6. washThe combined chloroform extracts are washed with water
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-16847070d393484a890e2ce81c4eaa82
Source dataset
uspto-grants-1984_04
Patent number
US04443466

Linked notes

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