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

HRID 1722981Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[NH:19][C:18]2=[O:28])=[C:13]([F:29])[CH:12]=1>>[Cl:10][C:11]1[C:16]([N+:1]([O-:4])=[O:2])=[CH:15][C:14]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[NH:19][C:18]2=[O:28])=[C:13]([F:29])[CH:12]=1

Participants

Reactant 3

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 189164113-(4-Chloro-2-fluorophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 183659053-(4-chloro-2-fluoro-5-nitrophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Conditions

Temperature: -15 °C

Procedure

A nitrating solution consisting of 2.2 ml of nitric acid and 24 ml of sulphuric acid is pre-cooled to -15° C. 9.26 g of 3-(4-chloro-2-fluorophenyl)-6 -trifluoromethyl-2,4(1H,3H)-pyrimidinedione are added portion wise to the solution while stirring. The mixture is stirred at 15° C. for 30 minutes and subsequently at room temperature for 1 hour. Thereafter, the mixture is poured onto 150 ml of ice-water and the resulting crystalline precipitate is filtered off. In this manner there is obtained 3-(4-chloro-2-fluoro-5-nitrophenyl)-6 -trifluoromethyl-2,4(1H,3H)-pyrimidinedione. m.p. 204° C.

Workup

stirringThe mixture is stirred at 15° C. for 30 minutes and subsequently at room temperature for 1 hour
filtrationthe resulting crystalline precipitate is filtered off

Sources & evidence

ORD record: ord-36d26f4d14b24580a2f226eedc5f934b
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859229

Reaction notes

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