1,1'-Oxalyldiimidazole → 5-Hydroxy-1,4-dihydroquinoxaline-2,3-dione

HRID 1188728Notes

Reaction equation

HRID 1188728 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](N1C=CN=C1)(=[O:18])[C:11](N1C=CN=C1)=[O:12]>O1CCCC1>[OH:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[NH:1][C:10](=[O:18])[C:11](=[O:12])[NH:8]2

Participants

4

Reactant 2

HCID 1004391,1'-OxalyldiimidazoleHCID 5799372,3-Diaminophenol

Product 1

HCID 451216145-Hydroxy-1,4-dihydroquinoxaline-2,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2,3-diaminophenol (50 g) and 1,1′-oxalyldiimidazole (92 g) and tetrahydrofurane (1.2 L) is refluxed 30 minutes. The solvent is removed under reduced pressure and the remaining solid taken into ethyl acetate. The organic phase is washed with 1M aqueous hydrochloric solution, dried over sodium sulphate and concentrated under vacuum. The crude solid obtained is recrystallised from dimethylformamide; yield: 14.8 g; MS: 177.1 (M−1); 1H NMR (DMSO-d6, 300 MHz): δ [ppm] 6.61 (m, 2H); 6.91 (ss, 1H), 10.21 (s (1H); 11.05 (s, 1H); 11.85 (s, 1H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. washThe organic phase is washed with 1M aqueous hydrochloric solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customThe crude solid obtained
  6. customis recrystallised from dimethylformamide

Sources & evidence

ORD record
ord-239e0b8a34114f0c8ee65cf28d09e67f
Source dataset
uspto-grants-2014_03
Patent number
US08674097B2

Reaction notes

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