Sodium Trifluoroacetate → HCID 53759503, compound

HRID 2226106Notes

Reaction equation

HRID 2226106 reaction equation
[F:1][C:2]([F:7])([F:6])C([O-])=O.[Na+].Br[C:10]1[C:15]2[O:16][C:17]([CH3:20])([CH3:19])[O:18][C:14]=2[C:13]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]([CH3:32])[C:22]2=[O:33])=[C:12]([F:34])[CH:11]=1>[Cu]I.CN(C)C(=O)C>[CH3:19][C:17]1([CH3:20])[O:16][C:15]2[C:10]([C:2]([F:7])([F:6])[F:1])=[CH:11][C:12]([F:34])=[C:13]([N:21]3[C:26](=[O:27])[CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[N:23]([CH3:32])[C:22]3=[O:33])[C:14]=2[O:18]1

Participants

5

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 18966276HCID 18966276, compound

Product 1

HCID 53759503HCID 53759503, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 6.0 g (0.044 mole) of sodium trifluoroacetate, 4.18 g (0.022 mole) of copper(I)iodide, and 40 mL of N,N-dimethylacetamide under a nitrogen atmosphere at 140 ° C is added 4.83 g (0.011 mole) of 3-(7-bromo-2,2-dimethyl-5-fluoro- 1,3-benzodioxol-4-yl)- 1 -methyl-6-trifluoromethyluracil (Example 3). The temperature is then raised to 150° C. at which the reaction mixture is stirred for three hours. After being cooled to ambient temperature, the reaction mixture is poured into ice and then extracted with diethyl ether. The combined extracts are dried over anhydrous magnesium sulfate and filtered. The filtrate is evaporated under reduced pressure, leaving a residue which is purified using column chromatography on silica gel. The product-containing fractions are combined and the solvent evaporated under reduced pressure, leaving 3-(2,2-dimethyl-5-fluoro-7-trifluoromethyl- 1,3-benzodioxol-4-yi)- 1 -methyl-6-trifluoromethyluracil as a residue.

Workup

  1. temperatureAfter being cooled to ambient temperature
  2. additionthe reaction mixture is poured into ice
  3. extractionextracted with diethyl ether
  4. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated under reduced pressure
  7. customleaving a residue which
  8. customis purified
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-367455da77ec471f941e0b8c2f4b6a15
Source dataset
uspto-grants-1994_09
Patent number
US05346881

Reaction notes

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