Hydantoin → 4-[(3,4-Dihydroxy-5-nitrophenyl)methylidene]-2,5-imidazolidindione

HRID 977203Notes

Reaction equation

HRID 977203 reaction equation
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17])[CH:12]=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:7]2[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]2)[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 10006HydantoinHCID 517165Ammonium AcetateHCID 57489573,4-Dihydroxy-5-nitrobenzaldehyde

Product 1

HCID 537716314-[(3,4-Dihydroxy-5-nitrophenyl)methylidene]-2,5-imidazolidindione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution containing 0.65 g of hydantoin, 0.92 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 0.15 g of ammonium acetate in 15 ml of acetic acid was refluxed overnight. The product was filtered and washed with acetic acid and 2-propanol. Yield 0.56 g (42%), mp >350° C.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe product was filtered
  3. washwashed with acetic acid and 2-propanol

Sources & evidence

ORD record
ord-6fc1472fda60493698c8091abf1734c9
Source dataset
uspto-grants-1997_03
Patent number
US05614541

Reaction notes

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