N,N-Dimethylaniline → HCID 54348876, compound

HRID 596226Notes

Reaction equation

HRID 596226 reaction equation
ON=C(C1C=CC=CC=1)C#N.CN(C)C1C=CC=CC=1.ClC(OC(Cl)(Cl)Cl)=O.Cl[C:30]([O:32][N:33]=[C:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:35]#[N:36])=[O:31].[CH:43]1([CH:46]([OH:48])[CH3:47])[CH2:45][CH2:44]1>C1C=CC=CC=1.O1CCOCC1.N1C=CC=CC=1>[CH:43]1([CH:46]([O:48][C:30]([O:32][N:33]=[C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:35]#[N:36])=[O:31])[CH3:47])[CH2:45][CH2:44]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 dropwise added 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. To the resultant mixture containing 2-chlorocarbonyloxyimino-2-phenylacetonitrile was dropwise added a solution of 1-cyclopropylethanol (1.4 g.) and pyridine (1.2 ml.) in benzene (10 ml.) under ice-cooling. 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 in turn washed with 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solvent was distilled off and 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. temperaturecooling
  4. stirringThe mixture was stirred for 2 hours at the same temperature, for 4 hours at room temperature
  5. waitto stand overnight
  6. washwashed with 1N hydrochloric acid, water
  7. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
  8. distillationThe solvent was distilled off and to the oily residue
  9. additionwas added a small amount of methanol
  10. filtrationthe precipitated crystals were collected by filtration
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-fd11530b36894fadb5acdf9dd622a51c
Source dataset
uspto-grants-1977_03
Patent number
US04010178

Reaction notes

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