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

HRID 275654Notes

Reaction equation

HRID 275654 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:18]=[C:17]([OH:19])[C:16]([Cl:20])=[CH:15][C:14]=2[F:21])[C:3]1=[O:22].[N+:23]([O-])([OH:25])=[O:24]>S(=O)(=O)(O)O>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[C:18]([N+:23]([O-:25])=[O:24])=[C:17]([OH:19])[C:16]([Cl:20])=[CH:15][C:14]=2[F:21])[C:3]1=[O:22]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 183150861-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxy-6-nitrophenyl)-2,4(1H,3H)-pyrimidinedioneYield 35.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

This compound was prepared in the manner of Step A of Example 1, using 3.8 grams (0.011 mole) of 1-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedione, 1.0 gram (0.011 mole) of 70% nitric acid, and 50 mL of sulfuric acid, yielding 1.5 grams of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in the manner of Step A of Example 1

Sources & evidence

ORD record
ord-466ca36d33df4e2e99af92d19e297fb1
Source dataset
uspto-grants-2002_03
Patent number
US06352958B1

Reaction notes

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