N,N-Dimethylaniline → HCID 54348876, compound

HRID 597691Notes

Reaction equation

HRID 597691 reaction equation
ON=C(C1C=CC=CC=1)C#N.CN(C)C1C=CC=CC=1.ClC(OC(Cl)(Cl)Cl)=O.[CH:29]1([CH:32]([OH:34])[CH3:33])[CH2:31][CH2:30]1.Cl[C:36]([O:38][N:39]=[C:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:41]#[N:42])=[O:37]>C1C=CC=CC=1.O1CCOCC1.N1C=CC=CC=1>[CH:29]1([CH:32]([O:34][C:36]([O:38][N:39]=[C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:41]#[N:42])=[O:37])[CH3:33])[CH2:31][CH2:30]1

Participants

9

Reactant 5

HCID 949N,N-DimethylanilineHCID 10426DiphosgeneHCID 699982-(Hydroxyimino)-2-phenylacetonitrileHCID 791041-CyclopropylethanolHCID 536547752-Chlorocarbonyloxyimino-2-phenylacetonitrile

Product 1

HCID 54348876HCID 54348876, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-hydroxyimino-2-phenylacetonitrile (2.2 g.) and dimethylaniline (1.80 g.) in a mixture of benzene (25 ml.) and dioxane (3 ml.) was added dropwise to a solution of trichloromethyl chloroformate (phosgene dimer) (1.5 g.) in benzene (20 ml.) under ice-cooling. The mixture was stirred for 3 hours at the same temperature and allowed to stand overnight. A solution of 1-cyclopropylethanol (1.4 g.) and pyridine (1.2 ml.) in benzene (10 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile. The mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature and allowed to stand overnight. The reaction mixture was then washed with 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solvent was distilled off and a small amount of methanol to the oily residue was added a small amount of methanol. The mixture was allowed to stand in a refrigerator and the precipitated crystals were collected by filtration and recrystallized from methanol to give 2-(1-cyclopropylethoxycarbonyloxyimino)-2-phenylacetonitrile (0.7 g.), mp 65° to 67° C.

Workup

  1. temperaturecooling
  2. waitto stand overnight
  3. stirringThe mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature
  4. waitto stand overnight
  5. washThe reaction mixture was then washed with 1N hydrochloric acid, water
  6. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. additiona small amount of methanol to the oily residue was added a small amount of methanol
  9. filtrationthe precipitated crystals were collected by filtration
  10. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fa1af1cfa90b45159d52e76e220e497e
Source dataset
uspto-grants-1977_03
Patent number
US04014915

Reaction notes

Loading…