Sodium Thiosulfate → HCID 67165552, compound

HRID 878826Notes

Reaction equation

HRID 878826 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[O:13][N:12]=[C:11]([C:14]3[CH:26]=[CH:25][C:17]([C:18]([NH:20][C:21](=[O:24])[O:22][CH3:23])=[O:19])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[I:32]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:29])([F:31])[F:30])[O:13][N:12]=[C:11]([C:14]3[CH:26]=[C:25]([I:32])[C:17]([C:18]([NH:20][C:21](=[O:24])[O:22][CH3:23])=[O:19])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 67163960HCID 67163960, compound

Product 1

HCID 67165552HCID 67165552, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a solution of 0.24 g of methyl N-[4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-methylbenzoyl]carbamate synthesized in Synthetic Example 19 and 0.12 g of N-iodosuccinimide in 3 mL of N,N-dimethylformamide, 0.0112 g of palladium (II) acetate was added, and stirred under nitrogen atmosphere at 100° C. for 4 hours. After the completion of the reaction, the reaction mixture was poured in a solution of 0.03 g of sodium thiosulfate in 30 mL of water, and extracted with ethyl acetate (30 mL×1), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (gradient of 0:1 to 3:2) to obtain 0.11 g of the aimed product as colorless resinous substance.

Workup

  1. additionwas added
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate (30 mL×1)
  4. dry with materialdried over saturated sodium chloride aqueous solution
  5. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  6. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-d2c84787c3304886a5055c166aa1941a
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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