Imidazole → HCID 15333518, compound

HRID 2393229Notes

Reaction equation

HRID 2393229 reaction equation
N1C=CN=C1.CN(C)C(Cl)=O.[CH3:12][N:13]([CH3:21])[C:14]([N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:15].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CC(C)=O.C(N(CC)CC)C>[Br-:22].[CH2:23]([N+:18]1[CH:19]=[CH:20][N:16]([C:14](=[O:15])[N:13]([CH3:21])[CH3:12])[CH:17]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6598Dimethylcarbamoyl ChlorideHCID 81731-Bromodecane2×HCID 30533521H-Imidazole-1-carboxamide, N,N-dimethyl-

Product 1

HCID 15333518HCID 15333518, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8471TriethylamineSolvent

Procedure

To 13.6 gm (0.2 mole) of imidazole (Aldrich Chemical Co., Milwaukee, Wis., 99%) and 20.2 gm of triethylamine (Aldrich, 99%) in 100 ml dry acetone (Fisher Scientific Co., Pittsburgh, Pa.) in a magnetically stirred 250 ml round bottom flask under dry nitrogen was added 21.5 gm (0.2 mole) dimethylcarbamyl chloride (Aldrich, 99%) dropwise over a 20 min. period from a side-arm pressure equalizing addition funnel. A white precipitate formed during the addition under conditions of mild exothermicity. The addition funnel was replaced with a reflux condenser and the reaction refluxed for a further one hour. After cooling to room temperature, the precipitate was isolated by Buchner filtration onto Wattman #1 paper, rinsed on the filter with acetone, and discarded. The combined filtrate and rinse acetone solution was divided into two equal parts, each containing 0.1 mole of 1-dimethylcarbamoylimidazole. To one of these parts was added 22.1 gm (0.1 mole) of 1-bromodecane (Aldrich 98%) and the solution refluxed for seven hours under dry nitrogen. The acetone was evaporated at water aspirator vacuum in a rotoevaporator to the point where two layers formed. The upper layer contained largely unreacted bromodecane and the lower yielded 12 gm (0.043 mole for a 21.4% theorical yield) of the imidazolium salt as a waxy solid upon cooling to 5° C. The purity and identity of this product was confirmed by proton and carbon NMR in deuterium oxide solution.

Workup

  1. additionaddition funnel
  2. customA white precipitate formed during the addition under conditions of mild exothermicity
  3. customThe addition funnel was replaced with a reflux condenser
  4. temperaturethe reaction refluxed for a further one hour
  5. customthe precipitate was isolated by Buchner filtration onto Wattman #1 paper
  6. washrinsed on the
  7. filtrationfilter with acetone
  8. washThe combined filtrate and rinse acetone solution
  9. temperaturethe solution refluxed for seven hours under dry nitrogen
  10. customThe acetone was evaporated at water
  11. customformed
  12. customthe lower yielded 12 gm (0.043 mole for a 21.4%

Sources & evidence

ORD record
ord-aedc8317b95843bd9cede6e62e08cb6d
Source dataset
uspto-grants-1998_09
Patent number
US05807668

Reaction notes

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