Potassium Carbonate → HCID 14324521, compound

HRID 1588389Notes

Reaction equation

HRID 1588389 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15]([C:19]1[O:23][N:22]=[C:21]([OH:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:15]([C:19]1[O:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[C:11]([F:14])([F:13])[F:12])[C:21](=[O:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 612132-Chloro-5-nitrobenzotrifluorideHCID 178441207HCID 178441207, compound

Product 1

HCID 14324521HCID 14324521, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After mixing 15 g of 2-chloro-5-nitrobenzotrifluoride, 11.3 g of 5-t-butyl-3-hydroxyisoxazole, 11.0 g of potassium carbonate, and 80 ml of dimethyl sulfoxide, the reaction was performed for 5 hours at 80° C. After the reaction was over, the reaction mixture was cooled and extracted with ethyl acetate and water. The organic phase thus formed was recovered and applied to silica gel column chromatography. The main product thus obtained was recrystallized from a mixture of methanol and water to provide 8.8 g of the desired product with a yield of 40.1%. The melting point thereof was 59° C. to 60° C.

Workup

  1. temperaturewas cooled
  2. extractionextracted with ethyl acetate and water
  3. customThe organic phase thus formed
  4. customwas recovered
  5. customThe main product thus obtained
  6. customwas recrystallized from a mixture of methanol and water

Sources & evidence

ORD record
ord-d9f2edf9340241068a03e0314de1cc09
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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