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

HRID 550403Notes

Reaction equation

HRID 550403 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]#[N:12].[Na+].[C:14](=[O:17])([O-])[O-].[NH4+:18].[NH4+].[OH2:20]>CCO>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]21[C:11](=[O:20])[NH:12][C:14](=[O:17])[NH:18]2

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 119832-IndanoneHCID 517111Ammonium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 2-indanone (3.0 g, 22.6 mmol), sodium cyanide (3.3 g, 67.3 mmol), and ammonium carbonate (22 g, 228 mol) in H2O (50 mL) and EtOH (50 mL) was heated to 70° C. for 3 h, then allowed to cool to ambient temperature. The precipitate was collected by filtration and washed with H2O (5×100 mL). Drying in vacuo afforded the title compound as a gray-brown solid. MS: m/z=202 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O (5×100 mL)
  4. customDrying in vacuo

Sources & evidence

ORD record
ord-e866fb8938b444a2879d4bb23751dd5f
Source dataset
uspto-grants-2011_05
Patent number
US07947678B2

Reaction notes

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