Nitric Acid → HCID 20688825, compound

HRID 1597177Notes

Reaction equation

HRID 1597177 reaction equation
[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[NH:15][C:14]2=[O:24])=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.[N+:25]([O-])([OH:27])=[O:26]>C(O)(=O)C>[F:1][C:2]1[C:12]([N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[NH:15][C:14]2=[O:24])=[C:11]([N+:25]([O-:27])=[O:26])[C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19889039HCID 19889039, compound

Product 1

HCID 20688825HCID 20688825, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-[7-Fluoro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (7.0 g) was added by portion to a mixture of acetic acid (30 ml) and fuming nitric acid (90 ml) at 0° C. After stirring for 1 hr at room temperature, the solution was mixed with ice-water (200 ml) and then extracted with ethyl acetate (60 ml×3). The organic layers were combined and washed with water (20 ml×2) and brine (20 ml), dried over sodium sulfate. After filtration and evaporation, the residue was recrystallized from methylene chloride (8.3 g).

Workup

  1. extractionextracted with ethyl acetate (60 ml×3)
  2. washwashed with water (20 ml×2) and brine (20 ml)
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and evaporation
  5. customthe residue was recrystallized from methylene chloride (8.3 g)

Sources & evidence

ORD record
ord-024f6b5d17434e3fbef07bba253fe3fd
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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