Water → 3-Amino-4,4-dimethyl-pent-2-endinitrile
Reaction equation
[CH3:1][C:2]([CH3:7])([C:5]#[N:6])[C:3]#[N:4].[C:8](#[N:10])[CH3:9].O>C1(C)C=CC=CC=1>[NH2:4][C:3]([C:2]([CH3:7])([CH3:1])[C:5]#[N:6])=[CH:9][C:8]#[N:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
A solution of potassium tert amylate in toluene (25%, 11.8 mL, 23 mmol) is added slowly to a solution of 2,2-Dimethyl-malononitrile (2.0 g, 21 mmol) and acetonitrile (1.2 mL, 23 mmol) in toluene (20 mL) at 40° C. under argon. The reaction mixture is stirred at 40° C. for 2 h and then cooled to 12° C. Water (5 mL) is added and the mixture is stirred at 20° C. for 15 min and at 2° C. for 30 min. Filtration, washing with cold water (10 mL) and drying under vacuum provides 2.30 g 3-Amino-4,4-dimethyl-pent-2-endinitrile. Yield: 80%: ESI-MS: 136 [M+H]+; 1H-NMR (DMSO-d6): 1.5, 4.1, 6.8 ppm.
Workup
- temperaturecooled to 12° C
- stirringthe mixture is stirred at 20° C. for 15 min and at 2° C. for 30 min
- filtrationFiltration
- washwashing with cold water (10 mL)
- customdrying under vacuum
Sources & evidence
- ORD record
- ord-872e29c7f8944cd694d3e1316f92f1ff
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865744B1
Reaction notes
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