Dimethylcarbamoyl Chloride → HCID 14231157, compound

HRID 1723077Notes

Reaction equation

HRID 1723077 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH3:7][N:8]([CH3:12])[C:9](Cl)=[O:10].C(N(CC)CC)C>C(#N)C.CCOCC>[CH3:7][N:8]([CH3:12])[C:9]([N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)=[O:10]

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 178418800HCID 178418800, compound

Product 1

HCID 14231157HCID 14231157, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution containing 4-methylimidazole (17.0 g, 0.25 mole), N,N-dimethylcarbamoyl chloride (27.0 g, 0.25 mole) and triethylamine (30 g, 0.30 mole) in acetonitrile (125 mL) is stirred at reflux for 20 hours. The reaction mixture is cooled, diluted with ether (1000 mL) and filtered. The filtrate is evaporated and the residue is distilled under reduced pressure to afford 1-dimethylcarbamoyl-4-methyl-imidazole, b.p. 104°-106° C./0.35 mm Hg.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customThe filtrate is evaporated
  5. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-6fe8d00bf40b411ca4d8ed7304b8cace
Source dataset
uspto-grants-1989_08
Patent number
US04859691

Reaction notes

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