Potassium Carbonate → HCID 14324519, compound

HRID 1588388Notes

Reaction equation

HRID 1588388 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](Cl)=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[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:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=2)[C:21](=[O:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 670525-Chloro-2-nitrobenzotrifluorideHCID 178441207HCID 178441207, compound

Product 1

HCID 14324519HCID 14324519, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

After mixing 15.0 g of 2-nitro-5-chlorobenzotrifluoride, 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 6 hours at 100° C. After the reaction was over, the reaction mixture was poured into ice-water and then extracted with ethyl acetate. The organic phase 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 4.1 g of the desired compound with a yield of 18.7%. The melting point thereof was 125° C. to 126° C.

Workup

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

Sources & evidence

ORD record
ord-b2334dd179a84a849b31d6fe6308f626
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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