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

HRID 597690

反応式

HRID 597690 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 1049Pyridine溶媒HCID 1140Toluene溶媒2 回HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e723dae864d24c19bf32dddbd5d5fe61
出典データセット
uspto-grants-1977_03
特許番号
US04014915

関連ノート

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