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

HRID 130577Notes

Reaction equation

HRID 130577 reaction equation
C([C:8](CC1C=CC=CC=1)([C:12]([O-])=[O:13])[C:9]([O-:11])=[O:10])C1C=CC=CC=1.[H-].[Na+].[C:24]1(=[C:30]([C:34]#[N:35])[C:31]([NH2:33])=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl.[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[C:34]([CH:30]1[C:24]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:8]([C:9]([O:11][CH2:43][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:10])[C:12](=[O:13])[NH:33][C:31]1=[O:32])#[N:35]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 24758Sodium hydrideHCID 2636542-Cyano-2-cyclohexylidene-acetamideHCID 73217902,2-Dibenzylpropanedioate

Product 1

HCID 11233094Benzyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate

Procedure

3.41 g of dibenzylmalonate, 30 ml of toluene and 0.58 g of 60% sodium hydride in mineral oil are placed in a 100 ml flask equipped with a magnetic stirrer, thermometer and condenser, in a nitrogen atmosphere. After 15 minutes, 1.97 g of cyclohexylidenecyanoacetamide are added. The reaction mixture is left under agitation for 6 hours at 25° C. and is then acidified with 36% HCl. The organic phase is separated and the solvent is evaporated under reduced pressure to obtain 3.18 g of benzyl 5-cyano-2,4-dioxo-3-azaspiro[5,5]undecane-1-carboxylate.

Workup

  1. customequipped with a magnetic stirrer
  2. waitThe reaction mixture is left under agitation for 6 hours at 25° C.
  3. customThe organic phase is separated
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-4dd83bc023b84ba9941774ac3e31fffb
Source dataset
uspto-grants-2008_06
Patent number
US07381823B2

Reaction notes

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