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

HRID 597690

반응식

HRID 597690 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 241Benzene용매HCID 1049Pyridine용매HCID 1140Toluene용매2회HCID 6386tert-Butanol용매

실험 절차

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, 1N 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.

후처리

  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, 1N 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

출처 및 근거

ORD 기록
ord-e723dae864d24c19bf32dddbd5d5fe61
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04014915

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