Trimethylsilyl cyanide → 2-Amino-3-phenoxypropanenitrile
Reaction equation
[O:1]([CH2:8][C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([C:15]#[N:16])(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:15]#[N:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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 vitridenide (NaH2AL1 [0-CH2 -CH2OCH3 ]2) at 70% in toluene (1,4 ml viz 0.5 eq) in 3 m 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%.
Workup
- temperatureThe reaction mixture is maintained at room temperature for 3 hours
- customAfter purification
- extractionby acid base extraction, there
Sources & evidence
- ORD record
- ord-08f0eae8166a46659121b025c61133eb
- Source dataset
- uspto-grants-1992_04
- Patent number
- US05103019
Reaction notes
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