Malononitrile → 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)N(C)C>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
- 145 °C
Procedure
To a 500 ml flask is charged 13.2 gm (0.2 mole) of malononitrile, 18.2 gm (0.2 mole) of sodium dicyanamide and 80 ml of tetramethylurea. The stirred mixture is heated at 145° C. for 2.5 hours; then cooled to about room temperature. The slurry is diluted with 300 ml 2-butanol and stirred in an ice bath for one hour. The solids are filtered, washed with 50 ml of 2-butanol. The product is dried overnight at 70° C. in a vacuum oven to yield 25.0 gm of 1-amino-1-cyanamido-2,2-dicyanoethylene, sodium salt, 80.7% pure or a 65.0% yield.
Workup
- temperaturethen cooled to about room temperature
- filtrationThe solids are filtered
- washwashed with 50 ml of 2-butanol
- customThe product is dried overnight at 70° C. in a vacuum oven
Sources & evidence
- ORD record
- ord-d5f9fe9dc8464c3daef4b31524dc6276
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05344955
Reaction notes
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