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

HRID 1188728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188728
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-239e0b8a34114f0c8ee65cf28d09e67f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674097B2

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