Sodium Cyanide → 2-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrile

HRID 968074

Reaktionsgleichung

Reaktionsgleichung von HRID 968074
[C-:1]#[N:2].[Na+].Cl.[CH3:5][NH:6][CH3:7].[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O.C1(C)C=CC=CC=1>[F:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]([N:6]([CH3:7])[CH3:5])[C:1]#[N:2])=[CH:11][CH:10]=1

Komponenten

7

Edukt 3

HCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 680234-Fluorobenzaldehyde

Produkt 1

HCID 113098562-(4-fluorophenyl)-2-(N,N-dimethylamino)acetonitrileAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 159952Benzyltributylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Into a 1 l four-necked flask equipped with a thermometer, a stirrer and a dropping funnel, 30.9 g (0.6 mol) of sodium cyanide, 85.7 g (1.05 mol) of dimethylamine hydrochloride, 1.2 g of benzyltri-n-butylammonium chloride and 200 ml of water were charged, and a solution comprising 62.1 g (0.5 mol) of 4-fluorobenzaldehyde and 150 ml of toluene, was dropwise added over a period of 30 minutes at from 20 to 30° C. with stirring, and then reacted at from 45 to 50° C. for 4 hours. After completion of the reaction, 200 ml of water was added, and the mixture was subjected to liquid separation. The organic layer was separated, washed with a 5% sodium hydrogen carbonate aqueous solution and water, and then dried over anhydrous sodium sulfate. Toluene was distilled off, and the obtained oily substance was distilled under reduced pressure to obtain 79.3 g (yield: 89%) of the desired compound (boiling point: 100-101° C./1 KPa).

Aufarbeitung

  1. additionwere charged
  2. customreacted at from 45 to 50° C. for 4 hours
  3. additionwas added
  4. customthe mixture was subjected to liquid separation
  5. customThe organic layer was separated
  6. washwashed with a 5% sodium hydrogen carbonate aqueous solution and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationToluene was distilled off
  9. distillationthe obtained oily substance was distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3c031abe23854ad29d09c9be99177859
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06956132B2

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