N,N-Dimethylaniline → HCID 85862764, compound

HRID 2082990Notes

Reaction equation

HRID 2082990 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 added dropwise to a solution of trichloromethyl chloroformate (phosgene dimer) (5.5 g.) in benzene (15 ml.) under ice-cooling. The mixture was stirred for 1 hour at the same temperature, for 2 hours at room temperature and then allowed to stand overnight. A solution of tert-butyl alcohol (5.6 g.) and pyridine (6.0 ml.) in benzene (20 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing benzophenone O-chlorocarbonyloxime. The mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. The reaction mixture was then 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 petroleum ether was added to the resulting crystals. 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 the pure compound, mp 131° to 133° C.

Workup

  1. temperaturecooling
  2. waitto stand overnight
  3. stirringThe mixture was stirred for 6 hours at the same temperature
  4. waitto stand overnight
  5. washThe reaction mixture was then washed with water, 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. additionpetroleum ether was added to the resulting crystals
  9. filtrationThe crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-dfdc2efc629548258ba98e21089ddfeb
Source dataset
uspto-grants-1978_04
Patent number
US04083848

Reaction notes

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