Hydrochloric Acid → 2-chloro-2-trifluoromethyl-3-[3-fluoro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoic acid
Reaction equation
N[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.[F:22][C:23]([F:30])([F:29])[C:24](=[CH2:28])[C:25]([OH:27])=[O:26].N([O-])=O.[Na+].[ClH:35]>CC(C)=O.[Cu]Cl>[Cl:35][C:24]([C:23]([F:30])([F:29])[F:22])([CH2:28][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([F:21])[CH:3]=1)[C:25]([OH:27])=[O:26]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
This compound was prepared in a manner analogous to that of Step E of Example 1, using 6.0 grams (0.020 mole) of 3-(4-amino-2-fluorophenyl)-1-methyl-6-trifluoromethyluracil (prepared as in Step D of Example 1), 28.0 grams (0.200 mole) of 2-trifluoromethylpropenoic acid, 1.4 grams (0.020 mole) of sodium nitrite, 0.5 gram (0.005 mole) of copper(I) chloride, and 30 mL of concentrated hydrochloric acid in 150 mL of acetone, yielding 5.8 grams of 2-chloro-2-trifluoromethyl-3-[3-fluoro-4-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl]propanoic acid. The NMR spectrum was consistent with the proposed structure. This reaction differed from Step E of Example 1 in that the intermediate propene used here was the acid, rather than the methyl ester, as was used in Step E of Example 1.
Workup
- customThis compound was prepared in a manner analogous to that of Step E of Example 1
Sources & evidence
- ORD record
- ord-d6ea0f260879416f8818340d23a895ba
- Source dataset
- uspto-grants-1994_05
- Patent number
- US05310723
Reaction notes
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