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

HRID 130576Notes

Reaction equation

HRID 130576 reaction equation
[CH3:1][O-].[Na+].C[C:5](C)([C:9]([O-:11])=[O:10])[C:6]([O-:8])=O.[Na].[C:14]1(=[C:20]([C:24]#[N:25])[C:21]([NH2:23])=[O:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>CO>[C:24]([CH:20]1[C:14]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:5]([C:9]([O:11][CH3:1])=[O:10])[C:6](=[O:8])[NH:23][C:21]1=[O:22])#[N:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2636542-Cyano-2-cyclohexylidene-acetamideHCID 5360545SodiumHCID 6946994DimethylmalonatHCID 10942334Sodium Methoxide

Product 1

HCID 11323033Methyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

24 ml of a 5.4 M solution of sodium methylate in methanol, 17.7 g of dimethylmalonate and 100 ml of methanol are placed in a 250 ml flask equipped with a mechanical stirrer, thermometer and condenser, under nitrogen flow. After 30 minutes, when the sodium has completely dissolved, a suspension of 20 g cyclohexylidenecyanoacetamide in 50 ml of methanol is added over a period of 15 minutes. The reaction mixture is left under agitation for 1 hour at 25° C. and is subsequently acidified with 5% HCl. The solid obtained is filtered off, washed with methanol and dried under vacuum. 28 g of methyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate are obtained.

Workup

  1. customequipped with a mechanical stirrer
  2. additionis added over a period of 15 minutes
  3. waitThe reaction mixture is left under agitation for 1 hour at 25° C.
  4. customThe solid obtained
  5. filtrationis filtered off
  6. washwashed with methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-5972a5f83f5847ec91864d1e973cb498
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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