Dimethyl Sulfoxide → HCID 14324509, compound

HRID 1588382Notes

Reaction equation

HRID 1588382 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]([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>O>[C:15]([C:19]1[O:23][N:22]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[C:21](=[O:24])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 178441207HCID 178441207, compound

Product 1

HCID 14324509HCID 14324509, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

After mixing 15.0 g of 4-chloro-3-nitrobenzotrifluoride, 11.3 g of 5-t-butyl-3-hydroxyisoxazole, 11.0 g of potassium carbonate, and 80 ml of dimethyl sulfoxide, the mixture was reacted for 4 hours at 80° C. After cooling, the reaction mixture obtained was poured into water to deposit crystals which were then recovered by filtration and recrystallized from a mixture of water and methanol to provide 10.0 g of the desired compound with a yield of 45.5%. The melting point thereof was 116° to 117° C.

Workup

  1. customthe mixture was reacted for 4 hours at 80° C
  2. temperatureAfter cooling
  3. customthe reaction mixture obtained
  4. filtrationwere then recovered by filtration
  5. customrecrystallized from a mixture of water and methanol

Sources & evidence

ORD record
ord-df7e43c8131841eaa41977e2db14665f
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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