N,N-Dimethylaniline → HCID 85862764, compound

HRID 596222Notes

Reaction equation

HRID 596222 reaction equation
[C:1](=[N:14][OH:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.Cl[C:26]([O:28]C(Cl)(Cl)Cl)=[O:27].ClC(ON=[C:38]([C:45]1[CH:50]=CC=C[CH:46]=1)C1C=CC=CC=1)=O>C1C=CC=CC=1.O1CCOCC1.N1C=CC=CC=1.C(O)(C)(C)C>[C:45]([O:28][C:26]([O:15][N:14]=[C:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:27])([CH3:38])([CH3:46])[CH3:50]

Participants

9

Reactant 4

HCID 949N,N-DimethylanilineHCID 10426DiphosgeneHCID 11324Benzophenone oximeHCID 11219144HCID 11219144, compound

Product 1

HCID 85862764HCID 85862764, compound

Reagents, catalysts & solvents 4

HCID 241BenzeneSolvent3×HCID 1049PyridineSolventHCID 6386tert-ButanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of benzophenone oxime (9.85 g.) and dimethylaniline (6.6 g.) in a mixture of benzene (50 ml.) and dioxane (10 ml.) was dropwise added to a solution of trichloromethyl chloroformate (phosgene dimer) (5.5 g.) in benzene (15 ml.) under ice-cooling, and the mixture was stirred for 1 hour at the same temperature, for 2 hours at room temperature and allowed to stand overnight. To the resultant mixture containing benzophenone O-chlorocarbonyloxime was dropwise added a solution of tert-butyl alcohol (5.6 g.) and pyridine (6.0 ml.) in benzene (20 ml.) under ice-cooling, and the mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. The reaction mixture was in turn washed with water, 1N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solvent was distilled off and to the resulting crystals was added petroleum ether. The crystals were collected by filtration and dried to give benzophenone O-tert-butoxycarbonyloxime (10.5 g.), mp 126° to 133° C. A small amount of the crystals was recrystallized from a mixture of toluene and petroleum ether to give pure compound, mp 131° to 133° C.

Workup

  1. temperaturecooling
  2. waitto stand overnight
  3. temperaturecooling
  4. stirringthe mixture was stirred for 6 hours at the same temperature
  5. waitto stand overnight
  6. washwashed with water, 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 resulting crystals
  9. additionwas added petroleum ether
  10. filtrationThe crystals were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-b3e5c3c19ee244bda5489ceffbb68a4f
Source dataset
uspto-grants-1977_03
Patent number
US04010178

Reaction notes

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