Dimethylcarbamoyl Chloride → 1-(N,N-Dimethylcarbamoyl)-4,5-dicyanoimidazole

HRID 27032

Reaction equation

HRID 27032 reaction equation
O1CCOCC1.[C:7]([C:9]1[N:10]=[CH:11][NH:12][C:13]=1[C:14]#[N:15])#[N:8].C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>>[CH3:23][N:24]([CH3:28])[C:25]([N:10]1[C:9]([C:7]#[N:8])=[C:13]([C:14]#[N:15])[N:12]=[CH:11]1)=[O:26]

Participants

5

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 707294,5-Dicyanoimidazole

Product 1

HCID 233434181-(N,N-Dimethylcarbamoyl)-4,5-dicyanoimidazole

Procedure

To 50 ml of dry 1,4-dioxane 6.0 g (0.05 mole) of 4,5-dicyanoimidazole, 5.0 g (0.05 mole) of triethylamine and 6.0 g (0.055 mole) of dimethylcarbamoyl chloride are added in succession at room temperature. This mixture is stirred and refluxed for 3 days, cooled to room temperature and evaporated to dryness. The residue is stirred in 50 ml of ethyl acetate and 50 ml water. The organic layer is separated, washed, dried and evaporated to give 8 g. (85%) of white product.

Workup

  1. temperaturerefluxed for 3 days
  2. customevaporated to dryness
  3. stirringThe residue is stirred in 50 ml of ethyl acetate
  4. customThe organic layer is separated
  5. washwashed
  6. customdried
  7. customevaporated
  8. customto give 8 g

Sources & evidence

ORD record
ord-ccbdcc529e104ca9a8cdaf4b5e1e4621
Source dataset
uspto-grants-1980_09
Patent number
US04220466

Linked notes

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