Dimethylcarbamoyl Chloride → HCID 14231157, compound

HRID 2108012Notes

Reaction equation

HRID 2108012 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.C(OCC)C>[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 (16.4 g), N,N-dimethylcarbamoyl chloride (30 g) and triethylamine (30 g) in acetonitrile (125 mL) is stirred at reflux for 20 hours. Upon cooling, the reaction is diluted with diethyl ether (1000 mL) and then filtered. The filtrate is concentrated and the residue is distilled under reduced pressure. 1-(Dimethylcarbamoyl)-4-methylimidazole is obtained as a colorless liquid, b.p. 104°-106° at 0.35 mm Hg.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureUpon cooling
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated
  5. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-bba7ec714f33407b8901aa23bf34aff5
Source dataset
uspto-grants-1990_06
Patent number
US04937250

Reaction notes

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