Hydrochloric Acid → HCID 66700868, compound

HRID 1253737Notes

Reaction equation

HRID 1253737 reaction equation
[OH:1]S(O)(=O)=O.[CH2:6]([N:13]1[CH2:30][CH2:29][CH2:28][C:16]2([CH:21](C#N)[C:20](=[O:24])N[C:18](=[O:25])[CH:17]2C#N)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-:31].[Na+].Cl>O>[CH2:6]([N:13]1[CH2:30][CH2:29][CH2:28][C:16]([CH2:17][C:18]([OH:25])=[O:1])([CH2:21][C:20]([OH:24])=[O:31])[CH2:15][CH2:14]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 667007972,4-Dioxo-9-(phenylmethyl)-3,9-diazaspiro[5.6]dodecane-1,5-dicarbonitrile

Product 1

HCID 66700868HCID 66700868, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

65% H2SO4 (17.5 ml) was added to a solid powder of 9-benzyl-2,4-dioxo-3,9-diazaspiro[5.6]dodecane-1,5-dicarbonitrile (3.5 g, 10.4 mmol) and the reaction mixture was heated at reflux for 2 h. Then the reaction mixture was cooled to RT, water (6.1 ml) was added and it was again heated at reflux for 20 h. After cooling to 0° C., the reaction mixture was first basified to pH ˜10-12 using 40% NaOH solution and then acidified to pH ˜2-3 using 2 N HCl solution. The solvent was removed under reduced pressure and the residue was dried by azeotropic distillation with benzene. Residual benzene was removed under reduced pressure to afford the dry solid product which was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperatureit was again heated
  4. temperatureat reflux for 20 h
  5. temperatureAfter cooling to 0° C.
  6. customThe solvent was removed under reduced pressure
  7. dry with materialthe residue was dried by azeotropic distillation with benzene
  8. customResidual benzene was removed under reduced pressure
  9. customto afford the dry solid product which
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-e9489ae95eaf4378af6ff2edacc362d3
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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