Nitric Acid → 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 1290629Notes

Reaction equation

HRID 1290629 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([F:21])[CH:3]=1.[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:22]([O-:24])=[O:23])=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 112557471-methyl-6-trifluoromethyl-3-(4-chloro-2-fluorophenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 111528343-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 3.0 grams (9.4 mmole) of 3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)pyrimidinedione in 30 mL of concentrated sulfuric acid was stirred and cooled in an ice bath. During 15 minutes, 0.75 mL (12 mmole) of aqueous 70% nitric acid was added dropwise, after which the reaction mixture was allowed to warm to ambient temperature, where it stirred for two hours. The reaction mixture was then poured into 150 mL of ice-water. The resulting precipitate was collected by filtration, washed with water, and dried under reduced pressure, yielding 3.0 grams of 3-(4-chloro-2-fluoro-5-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-fc37fb2ec4fb42989aba163c8fefa6ee
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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