Ethanol → 1',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione

HRID 1175676Notes

Reaction equation

HRID 1175676 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=O.[C:11](=[O:14])([O-])[O-].[NH4+:15].[NH4+:16].[C-]#N.[Na+].[CH2:20]([OH:22])C>O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]21[C:20](=[O:22])[NH:16][C:11](=[O:14])[NH:15]2

Participants

6

Reactant 4

HCID 702EthanolHCID 8929Sodium CyanideHCID 119832-IndanoneHCID 517111Ammonium Carbonate

Product 1

HCID 2799991',3'-dihydrospiro[imidazolidine-4,2'-indene]-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-indanone (67.8 mmol, 9 g) and ammonium carbonate (684 mmol, 66 g) in ethanol (150 ml) and water (150 ml) was added NaCN (201.9 mmol, 9.9 g) and the reaction mixture was stirred at 70° C. for 3 h. The reaction mixture was cooled to 0° C. and the precipitated product was filtered, washed with water (4×) and desiccated. LC/MS (10% to 99%): M/Z (M+H)+ (obs)=203; tR=1.78.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe precipitated product was filtered
  3. washwashed with water (4×)

Sources & evidence

ORD record
ord-f9f326e458494cd29b0bbc189ea85939
Source dataset
uspto-grants-2010_11
Patent number
US07842686B2

Reaction notes

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