Dimethyl Sulfoxide → HCID 14324547, compound

HRID 1588394Notes

Reaction equation

HRID 1588394 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]1([C:21]2[O:25][N:24]=[C:23]([OH:26])[CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[C:15]1([C:21]2[O:25][N:24]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[C:23](=[O:26])[CH:22]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 178515569HCID 178515569, compound

Product 1

HCID 14324547HCID 14324547, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After mixing 22.6 g of 4-chloro-3-nitrobenzotrifluoride, 19.3 g of 5-phenyl-3-hydroxyisoxazole, 16.8 g of potassium carbonate, and 150 ml of dimethyl sulfoxide, the reaction was performed for 3 hours at 70° C. After the reaction was over, the reaction mixture was cooled and poured into water. Crystals thus deposited were recovered by filtration and recrystallized from a mixture of dimethylformamide and methanol to provide 28.4 g of the desired product with a yield of 95.0%. The melting point thereof was 185° C. to 187° C.

Workup

  1. temperaturewas cooled
  2. filtrationCrystals thus deposited were recovered by filtration
  3. customrecrystallized from a mixture of dimethylformamide and methanol

Sources & evidence

ORD record
ord-84976c0ce0db42409e59e895f608a23e
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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