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]>CO>[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
- 22.5 °C
Procedure
98 g (1 mol) of cyclohexanone and 226 g (2 mol) of ethyl cyanoacetate were reacted with 204 g aqueous ammonia (equivalent to 3 mol of ammonia gas) in a solvent of methanol. After reacted at −5° C. to 0° C. for 24 hours, the reaction mixture was heated to 20 to 25° C. and stirred for 24 hours, and then heated to 60° C. Water is added in an amount equal to methanol, and the mixture was adjusted to pH 2-3 with sulfuric acid. The mixture was then cooled 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° C. to 0° C. for 24 hours
- temperatureheated to 60° C
- temperatureThe mixture was then cooled 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-2a00a6bcd4e74010807733a873c00a95
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07667071B2
Reaction notes
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