Reaktion #364599

ord-7850481a5cd84e0a9ed9330a8fabd701

Reaktionsgleichung

CCOC(=O)Nc1cc(-n2c(=O)cc(C(F)(F)F)[nH]c2=O)c(F)cc1Cl
3-(4Chloro-5-ethoxycarbonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione
O=S(=O)(O)O
sulfuric acid
O=[N+]([O-])O
nitric acid
O=S(=O)(O)O
sulfuric acid
→
CCOC(=O)Nc1c(Cl)cc(F)c(-n2c(=O)cc(C(F)(F)F)[nH]c2=O)c1[N+](=O)[O-]
3-(4-chloro-3-ethoxycarbonylamino-6-fluoro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Edukte

CCOC(=O)Nc1cc(-n2c(=O)cc(C(F)(F)F)[nH]c2=O)c(F)cc1Cl
3-(4Chloro-5-ethoxycarbonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione
O=S(=O)(O)O
sulfuric acid
O=[N+]([O-])O
nitric acid
O=S(=O)(O)O
sulfuric acid

Reagenzien

Keine

Lösungsmittel

—
ice water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONwas dropwise added
  2. 2
    Sonstigeformed immediately which
  3. 3
    Filtrationwas filtered
  4. 4
    Waschenwashed with water
  5. 5
    Sonstigedried in fume hood overnight (0.5 g)

Vorschrift

3-(4Chloro-5-ethoxycarbonylamino-2-fluorophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (XLVII) (1.0 g) was stirred with sulfuric acid (2 ml) at 0° C., then a mixture of nitric acid (1 ml) and sulfuric acid (1 ml) was dropwise added. After stirring at room temperature for 3 hr, it was poured into ice water (50 ml) and yellow crystals formed immediately which was filtered, washed with water and dried in fume hood overnight (0.5 g).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06355799B1uspto-grants-2002_03