Trimethylsilyl cyanide → 2-Amino-3-phenoxypropanenitrile

HRID 2165893

Reaktionsgleichung

Reaktionsgleichung von HRID 2165893
[O:1]([CH2:8][C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.COCCO[AlH2-]OCCOC.[Na+].C[Si]([C:27]#[N:28])(C)C>C1(C)C=CC=CC=1>[NH2:10][CH:9]([CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:27]#[N:28]

Komponenten

5

Edukt 3

HCID 82115Trimethylsilyl cyanideHCID 241641PhenoxyacetonitrileHCID 16684438Red-Al

Produkt 1

HCID 139832712-Amino-3-phenoxypropanenitrileAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

10 millimoles (1.33 g) of phenoxyacetonitrile are dissolved in 10 ml of anhydrous toluene at 0° C., under an argon atmosphere. A solution of vitride (NaH2Al[O-CH2 -CH2OCH3 ]2) at 70% in toluene (1,4 ml viz 0.5 eq) in 3 ml of anhydrous toluene is added, dropwise, at this temperature. The stirring is maintained for 1 hour at 0° C., then 2 ml (1.5 eq) of trimethylsilyl cyanide are added. The reaction mixture is maintained at room temperature for 3 hours, while stirring, then hydrolyzed by usual way. After purification by acid base extraction, there are obtained 0.300 g of -2-amino-3-phenoxy propionitrile with a yield of 20%.

Aufarbeitung

  1. temperatureThe reaction mixture is maintained at room temperature for 3 hours
  2. customAfter purification
  3. extractionby acid base extraction, there

Quellen und Nachweise

ORD-Eintrag
ord-d350f374911c4664977c99780b45af41
Quelldatensatz
uspto-grants-1990_07
Patentnummer
US04942221

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