Water → HCID 67164156, compound

HRID 878839Notes

Reaction equation

HRID 878839 reaction equation
BrC[C:3]1[CH:12]=[C:11]([C:13]2[CH2:17][C:16]([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[C:24]([Cl:29])[CH:23]=3)([C:18]([F:21])([F:20])[F:19])[O:15][N:14]=2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].Cl.[CH3:31]NC.C([N:36]([CH2:39][CH3:40])CC)C.O>CN(C)C=O>[Cl:29][C:24]1[CH:23]=[C:22]([C:16]2([C:18]([F:20])([F:19])[F:21])[O:15][N:14]=[C:13]([C:11]3[CH:12]=[CH:3][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:9]([C:39]([CH3:40])([CH3:31])[NH2:36])[CH:10]=3)[CH2:17]2)[CH:27]=[C:26]([Cl:28])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 58200176HCID 58200176, compound

Product 1

HCID 67164156HCID 67164156, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a solution of 1.50 g of methyl 2-bromomethyl-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoate in 20 mL of N,N-dimethylformamide, 0.48 g of dimethylamine hydrochloride and 1.48 g of triethylamine were added, and stirred at room temperature for 2 hours. After the completion of the reaction, 20 mL of water was added in the reaction mixture, and extracted with ethyl acetate (20 mL×2). The combined organic phases were 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 were eluated with ethyl acetate-hexane (1:3) to obtain 1.35 g of the aimed product as colorless resinous substance.

Workup

  1. additionwas added in the reaction mixture
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. dry with materialdried over saturated sodium chloride aqueous solution
  4. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  5. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-f54831fb57c643c98e25b67dbb228fd7
Source dataset
uspto-grants-2015_03
Patent number
US08987464B2

Reaction notes

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