Ammonia → 2,4-Dioxo-3-azaspiro(5.5)undecane-1,5-dicarbonitrile
Reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([CH2:10][C:11]([O:13]CC)=O)#[N:9].[NH3:16].S(=O)(=O)(O)O.[OH2:22]>C(O)C>[C:11]([CH:10]1[C:1]2([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:10]([C:8]#[N:9])[C:11](=[O:13])[NH:9][C:8]1=[O:22])#[N:16]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
98 g (1 mol) of cyclohexanone and 282.5 g (2.5 mol) of ethyl cyanoacetate were reacted with 340 g aqueous ammonia (equivalent to 5 mol of ammonia gas) in a solvent of ethanol. After reacted at 5 to 10° C. for 24 hours, the mixture was heated to 25° C. and stirred for another 24 hours. The temperature was raised to 60° C. and water was added in an amount equivalent to the ethanol. The pH value was adjusted to 2 to 3 with sulfuric acid. The temperature was lowered to below 5° C. and the precipitated 1,5-dicyano-2,4-dioxo-3-azaspiro[5,5]-undecane was collected by filtration.
Workup
- customAfter reacted at 5 to 10° C. for 24 hours
- temperatureThe temperature was raised to 60° C.
- customwas lowered to below 5° C.
- filtrationthe precipitated 1,5-dicyano-2,4-dioxo-3-azaspiro[5,5]-undecane was collected by filtration
Sources & evidence
- ORD record
- ord-cbd808bda9c14b2cb8f65b4e844c8783
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07667071B2
Reaction notes
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