Dimethyl Sulfoxide → 4-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

HRID 1848316Notes

Reaction equation

HRID 1848316 reaction equation
CS(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([C:27]([F:30])([F:29])[F:28])=[CH:14][C:15]([C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:26])[CH:18]=2)=O)[CH:9]=[C:10]([Cl:12])[CH:11]=1.C1(C)C=CC=CC=1.[OH2:38].S(O)(O)(=O)=O.[NH2:44]O>[OH-].[Na+]>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:27]([F:30])([F:29])[F:28])[O:38][N:44]=[C:15]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[C:19]([CH3:26])[CH:18]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962Water2×HCID 1140Toluene2×HCID 159255Hydroxylamine, sulfate (1:1)HCID 667352444-(3-(3,5-Dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid

Product 1

HCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

6.27 g of dimethylsulfoxide was added to solution in which 1.61 g of 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl)-2-methylbenzoic acid was dissolved into 10.5 g of toluene, and the mixture was cooled to 0° C. A solution in which 0.64 g of sodium hydroxide was dissolved into 1.6 g of water was carefully added to the mixtures so that the temperature of the reaction solution did not exceed 5° C. Moreover, a solution in which 0.46 g of hydroxylamine sulfate was dissolved into 2.24 g of water was carefully added to the mixtures so that the temperature of the reaction solution did not exceed 5° C. The reaction was performed for 1 hour with stirring while keeping the reaction temperature at 0° C. The reaction solution was analyzed by high-performance liquid chromatography (detected by UV detector at a wavelength of 254 nm, and calculated with omitting the peak of toluene). The target product of 4-(5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid was produced in 85.0% of relative area.

Workup

  1. additionwas carefully added to the mixtures so that the temperature of the reaction solution
  2. customdid not exceed 5° C
  3. additionwas carefully added to the mixtures so that the temperature of the reaction solution
  4. customdid not exceed 5° C
  5. customat 0° C

Sources & evidence

ORD record
ord-c0787bb340384021938e00dea308056c
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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