Reaktion #64211

Reaktionsgleichung

ammonia

ammonium chloride

sodium cyanide

ammonia

2-[4-(1,1-dimethylethyl)phenoxy]acetoaldehyde

→

2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propionitrile

Lösungsmittel

water

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThen the reaction mixture was further stirred at the same temperature for 30 minutes
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe residue was washed with water
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

To a mixture of 2.92 g (54.6 mmol.) of ammonium chloride, 2.47 g (50.4 mmol.) of sodium cyanide and 18 ml (296 mmol.) of a 28% aqueous solution of ammonia, there was added dropwise a solution of the wet cake of 2-[4-(1,1-dimethylethyl)phenoxy]acetoaldehyde obtained in Production Example 9 in 8 ml of methanol with stirring at a temperature of 10° C. for 30 minutes. Then the reaction mixture was further stirred at the same temperature for 30 minutes. Then, the reaction mixture was stirred under an atmosphere of a gas of ammonia at room temperature for 2 days. After the reaction was completed, the resultant mixture was poured into cold water and extracted with ethyl acetate. The residue was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography to give 3.89 g of 2-amino-3-[4-(1,1-dimethylethyl)phenoxy]propionitrile as a light-yellowish resinoid [60 MHz 1H-NMR (CDCl3, TMS), δ (ppm) 1.26(9H,s), 4.05(2H,d, J=5Hz), 4.63(1H,t, J=5Hz), 6.72(2H,d, J=10Hz), 7.21(2H,d, J=10Hz)].

Quelle