Dimethylformamide → Cyanamide, (1-amino-2,2-dicyanoethenyl)-
Reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[N-:6]([C:9]#[N:10])[C:7]#[N:8].[Na+].CN(C)C=O>CC(O)CC>[NH2:8][C:7]([NH:6][C:9]#[N:10])=[C:2]([C:1]#[N:5])[C:3]#[N:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 168 °C
Procedure
To a 250 ml flask is charged 6.6 gm (0.1 mole) of malononitrile, 8.9 gm (0.1 mole) of sodium dicyanamide and 40 ml of dimethyl formamide. The stirred mixture is heated to reflux (168° C.) and held 15 minutes; then cooled to about room temperature. Then 150 ml 2-butanol is added and the stirred mixture is cooled in an ice bath. The solids are filtered, washed with 2-butanol and dried overnight in a vacuum oven. There is obtained 11.4 gm of 1-amino-1-cyanamido-2,2-dicyanoethylene, sodium salt, 81.2% pure, or a 59.7% yield.
Workup
- temperatureThe stirred mixture is heated
- temperaturethen cooled to about room temperature
- temperaturethe stirred mixture is cooled in an ice bath
- filtrationThe solids are filtered
- washwashed with 2-butanol
- customdried overnight in a vacuum oven
Sources & evidence
- ORD record
- ord-7bfd476473484a25b64bf82f07c24a81
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344955
Reaction notes
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