Hydrochloric Acid → Ethyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

HRID 130575Notes

Reaction equation

HRID 130575 reaction equation
[Na].C([C:4](CC)([C:8]([O-:10])=O)[C:5]([O-:7])=[O:6])C.[C:13]1(=[C:19]([C:23]#[N:24])[C:20]([NH2:22])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl.[CH2:26](O)[CH3:27]>>[C:23]([CH:19]1[C:13]2([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:4]([C:5]([O:7][CH2:26][CH3:27])=[O:6])[C:8](=[O:10])[NH:22][C:20]1=[O:21])#[N:24]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2636542-Cyano-2-cyclohexylidene-acetamideHCID 5360545Sodium2×HCID 69515632,2-Diethylpropanedioate

Product 1

HCID 3408334Ethyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

Procedure

0.69 g of sodium metal are suspended in 30 ml of anhydrous ethanol in a 100 ml flask equipped with a magnetic stirrer, thermometer and condenser, in a nitrogen atmosphere. When the sodium has dissolved, 4.8 g of diethylmalonate are added followed, after 15 minutes, by 4.92 g of cyclohexylidenecyanoacetamide. The mixture is left for 1 hour under agitation at 25° C. and then acidified with 36% HCl. The solid obtained is filtered off and dried under vacuum. 6.84 g of ethyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate are obtained.

Workup

  1. customequipped with a magnetic stirrer
  2. customThe solid obtained
  3. filtrationis filtered off
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1646ed45e59a44df9b0662552ef8cefa
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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