Dimethyl Sulfoxide → HCID 14324539, compound

HRID 1588392Notes

Reaction equation

HRID 1588392 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]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:29][N:28]=[C:27]([OH:30])[CH:26]=2)=[CH:21][CH:20]=1)(=[O:17])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[C:15]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:29][N:28]([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:27](=[O:30])[CH:26]=2)=[CH:23][CH:24]=1)(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 178474091HCID 178474091, compound

Product 1

HCID 14324539HCID 14324539, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After mixing 6.4 g of 4-chloro-3-nitrobenzotrifluoride, 7.0 g of 5-(4-acetylaminophenyl)-3-hydroxyisoxazole, 4.5 g of potassium carbonate, and 50 ml of dimethyl sulfoxide, the reaction was performed for 5 hours at 70° C. After the reaction was over, the reaction mixture obtained was poured into water and crystals thus formed were recovered by filtration and recrystallized from a mixture of dimethylformamide and methanol to provide 8.8 g of the desired product with a yield of 75.9%. The melting point thereof was 238° C. to 239° C.

Workup

  1. customobtained
  2. customthus formed
  3. filtrationwere recovered by filtration
  4. customrecrystallized from a mixture of dimethylformamide and methanol

Sources & evidence

ORD record
ord-0d1b1aaffcd14d9a838149ee9967f721
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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