Ethyl cyanoacetate → 2,4-Dioxo-3-azaspiro(5.5)undecane-1,5-dicarbonitrile

HRID 1446372Notes

Reaction equation

HRID 1446372 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].[C:16]([CH2:18][C:19]([NH2:21])=[O:20])#[N:17].C(N(CC)CC)C>CO>[C:16]([CH:18]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:21][C:19]1=[O:20])#[N:17]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 7898CyanoacetamideHCID 7967CyclohexanoneHCID 8471Triethylamine

Product 1

HCID 203662,4-Dioxo-3-azaspiro(5.5)undecane-1,5-dicarbonitrileYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

98 g (1 mol) of cyclohexanone, 113 g (1 mol) of ethyl cyanoacetate, 84 g (1 mol) of cyanoacetamide, and 100 ml of methanol were mixed in a reaction flask. 101 g (1 mol) of triethylamine was added dropwise under stirring, and the reaction mixture was stirred for 8 hours with the temperature controlled within the range of 25° C. to 30° C., and then was cooled and filtered. The filter cake was suspended in water, and the suspension was adjusted to pH 2-3 with concentrated hydrochloric acid while stirring. The suspension was filtered, washed with water, and dried to provide 1,5-dicyano-2,4-dioxo-3-azaspiro[5,5]-undecane. Yield: 88%, melting point: 202 to 210° C.

Workup

  1. stirringthe reaction mixture was stirred for 8 hours with the temperature
  2. customcontrolled within the range of 25° C. to 30° C.
  3. temperaturewas cooled
  4. filtrationfiltered
  5. stirringwhile stirring
  6. filtrationThe suspension was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-85496ac01932412cab66b043534fe172
Source dataset
uspto-grants-2010_02
Patent number
US07667071B2

Reaction notes

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