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

HRID 588988Notes

Reaction equation

HRID 588988 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>[CH2:3]1[C:2]2([NH:18][C:14](=[O:17])[NH:12][C:11]2=[O:20])[CH2:1][C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=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 (250 g, 1.89 mol), sodium cyanide (278 g, 5.68 mol) and ammonium carbonate (1.81 kg, 18.9 mol) in H2O (1.5 L) and EtOH (1.5 L) was heated at 70° C. for 3 h, then allowed to cool to ambient temperature. The precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the title compound. MS: m/z=202.0 (M+1).

Workup

  1. temperatureto cool to ambient temperature
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6d72de8b7877407499c58040130bc6f2
Source dataset
uspto-grants-2016_01
Patent number
US09227973B2

Reaction notes

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