Oxalic acid dihydrate → 6-Chloro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 53784

Reaktionsgleichung

Reaktionsgleichung von HRID 53784
[NH2:1][C:2]1[CH:3]=[C:4]([C:10]([F:13])([F:12])[F:11])[C:5]([Cl:9])=[CH:6][C:7]=1[NH2:8].O.O.[C:16](O)(=[O:20])[C:17](O)=[O:18]>Cl.[OH-].[Na+]>[Cl:9][C:5]1[CH:6]=[C:7]2[C:2](=[CH:3][C:4]=1[C:10]([F:13])([F:11])[F:12])[NH:1][C:17](=[O:18])[C:16](=[O:20])[NH:8]2

Komponenten

5

Edukt 2

HCID 61373Oxalic acid dihydrateHCID 27734974-Chloro-5-(trifluoromethyl)benzene-1,2-diamine

Produkt 1

HCID 106116896-Chloro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedioneAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A mixture of 3,4-diamino-6-chlorobenzotrifluoride (185 mg, 0.88 mmol) and oxalic acid dihydrate (117 mg, 0.93 mmol, used as received) in 2N HCl (4 mL) was refluxed at 170°-5° C. for 3 h, then cooled to room temperature. The mixture was centrifuged and the liquid layer was removed. The yellow solid was washed twice by cold water (2×2 mL), collected by filtration, and dried at 60° C. with reduced pressure for 2 h, affording 180 mg of crude title compound (77.3% ) as a light yellow powder. The crude product was dissolved in 1N NaOH (6 mL) and filtered. The filtrate was acidified to pH=6, affording 138 mg of title compound. It was recrystallized from DMSO/H2O twice to give 102 mg of pure compound (43.9%) as yellow microcrystals. mp: >360° C. (dec. from 295° C.). IR (KBr, cm-1) 3425, 3200, 1731, 1706, 1625; 1400. 1H NMR (DMSO-d6): δ 7.274 (s, 1H); 7.478 (s, 1H); 12.145 (s, 2H). HRMS: calcd for C9H4ClF3N2O2 (M+) m/z: 263.9912; found: 263.9919.

Aufarbeitung

  1. temperaturewas refluxed at 170°-5° C. for 3 h
  2. customthe liquid layer was removed
  3. washThe yellow solid was washed twice by cold water (2×2 mL)
  4. filtrationcollected by filtration
  5. customdried at 60° C. with reduced pressure for 2 h
  6. customaffording 180 mg of crude title compound (77.3% ) as a light yellow powder
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-8bebdfe0c43c4736a10e9179daa18a5a
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620979

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