N,N-Dimethylaniline → 2-Tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile

HRID 1578214

Reaktionsgleichung

Reaktionsgleichung von HRID 1578214
[OH:1][N:2]=[C:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].CN(C)C1C=CC=CC=1.Cl[C:26]([O:28]C(Cl)(Cl)Cl)=[O:27].ClC(ON=C([C:41]1[C:50]2[C:45](=CC=C[CH:49]=2)C=CC=1)C#N)=O>C1(C)C=CC=CC=1.C1C=CC=CC=1.N1C=CC=CC=1.C(O)(C)(C)C>[C:50]([O:28][C:26]([O:1][N:2]=[C:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5])=[O:27])([CH3:49])([CH3:41])[CH3:45]

Komponenten

9

Edukt 4

HCID 949N,N-DimethylanilineHCID 10426DiphosgeneHCID 543473962-Chlorocarbonyloxyimino-2-(1-naphthyl)acetonitrileHCID 736804482-Hydroxyimino-2-(1-naphthyl)acetonitrile

Produkt 1

HCID 537899872-Tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 241BenzeneLösungsmittelHCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A solution of 2-hydroxyimino-2-(1-naphthyl)acetonitrile (7.0 g.) and dimethylaniline (12.0 g.) in toluene (100 ml.) was added dropwise, under ice-cooling, to a solution of trichloromethyl chloroformate (phosgene dimer) (3.56 g.) in benzene (30 ml.). The mixture was stirred for 3 hours at the same temperature and allowed to stand overnight. A solution of tert-butyl alcohol (11.1 g.) and pyridine (12 ml.) in toluene (20 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing 2-chlorocarbonyloxyimino-2-(1-naphthyl)acetonitrile. The mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. The reaction mixture was then washed with water, 1 N hydrochloric acid, water, a sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate. The solution was concentrated under reduced pressure and n-hexane and methanol were added to the residue. The mixture was allowed to stand in a refrigerator and the precipitated crystals were collected by filtration and recrystallized twice from methanol to give 2-tert-butoxycarbonyloxyimino-2-(1-naphthyl)acetonitrile (3.3 g.), mp 90° to 92° C.

Aufarbeitung

  1. waitto stand overnight
  2. stirringThe mixture was stirred for 6 hours at the same temperature
  3. waitto stand overnight
  4. washThe reaction mixture was then washed with water, 1 N hydrochloric acid, water
  5. dry with materiala sodium bicarbonate aqueous solution and water, and dried over magnesium sulfate
  6. concentrationThe solution was concentrated under reduced pressure and n-hexane and methanol
  7. additionwere added to the residue
  8. filtrationthe precipitated crystals were collected by filtration
  9. customrecrystallized twice from methanol

Quellen und Nachweise

ORD-Eintrag
ord-ee901ca740a64ef7b65533106e6cf638
Quelldatensatz
uspto-grants-1981_09
Patentnummer
USRE030752

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