Acetone → 1,3-Bis(dimethylcarbamoyl)-1H-imidazol-3-ium chloride

HRID 1450126Notes

Reaction equation

HRID 1450126 reaction equation
[CH3:1][N:2]([CH3:6])[C:3]([Cl:5])=[O:4].[NH:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.[CH2:12]([N:14]([CH2:17]C)[CH2:15]C)C.CC(C)=[O:21]>>[Cl-:5].[CH3:1][N:2]([CH3:6])[C:3]([N+:7]1[CH:11]=[CH:10][N:9]([C:12](=[O:21])[N:14]([CH3:17])[CH3:15])[CH:8]=1)=[O:4]

Participants

5

Reactant 4

HCID 180AcetoneHCID 795ImidazoleHCID 6598Dimethylcarbamoyl ChlorideHCID 8471Triethylamine

Product 1

HCID 30778511,3-Bis(dimethylcarbamoyl)-1H-imidazol-3-ium chloride

Procedure

10.75 g (0.1 mole) dimethylcarbamoyl chloride are added dropwise with stirring to a solution of 6.8 g. (0.1 mole) imidazole and 11 g. triethylamine in 70 ml dry acetone. On warming, triethyl- ammonium chloride precipitates. After 5 hours standing at room temperature, the reaction mixture is filtered and 10.75 g. dimethyl- carbamoyl chloride is added again to the filtrate. After 2 days at room temperature, the crystalline product is filtered off, washed with acetone, and vacuum dried. Yield: 20.2 g 1,3-bis-(dimethylcarbamoyl)-imidazolium chloride (77% of theoretical), melting point 115° C. Analysis:

Workup

  1. temperatureOn warming
  2. customtriethyl- ammonium chloride precipitates
  3. filtrationthe reaction mixture is filtered
  4. additiondimethyl- carbamoyl chloride is added again to the filtrate
  5. waitAfter 2 days at room temperature
  6. filtrationthe crystalline product is filtered off
  7. washwashed with acetone, and vacuum
  8. customdried

Sources & evidence

ORD record
ord-d15064b822c94d2a9a6352fd7c3ce996
Source dataset
uspto-grants-1997_02
Patent number
US05601971

Reaction notes

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