Dimethylformamide dimethyl acetal → HCID 152771638, compound

HRID 552656Notes

Reaction equation

HRID 552656 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH2:23][O:24][CH3:25])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:30][O:31][CH:32](OC)[N:33](C)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:27])([F:29])[F:28])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20][C:32]([O:31][CH3:30])=[NH:33])=[O:19])=[C:16]([CH2:23][O:24][CH3:25])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67164677HCID 67164677, compound

Product 1

HCID 152771638HCID 152771638, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 0.09 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methoxymethyl benzoic acid amide in 2 mL of tetrahydrofuran, 0.05 g of N,N-dimethylformamide dimethylacetal was added, and stirred at room temperature for 2 hours. After the completion of the reaction, the solvent was distilled off under reduced pressure, and the residue was dissolved in 2 mL of tetrahydrofuran, a solution of 0.02 g of methoxyamine hydrochloride in 2 mL of water was added dropwise. After the completion of the addition dropwise, it was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the solvent was distilled off under reduced pressure, 5 mL of water was added in the residue, and extracted with ethyl acetate (10 mL×1). The organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sulfuric acid, 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 (1:4) to obtain 0.07 g of the aimed product as white crystal.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in 2 mL of tetrahydrofuran
  4. additiona solution of 0.02 g of methoxyamine hydrochloride in 2 mL of water was added dropwise
  5. additionAfter the completion of the addition dropwise
  6. stirringto stir at room temperature further for 30 minutes
  7. customAfter the completion of the reaction
  8. distillationthe solvent was distilled off under reduced pressure, 5 mL of water
  9. additionwas added in the residue
  10. extractionextracted with ethyl acetate (10 mL×1)
  11. dry with materialdried over saturated sodium chloride aqueous solution
  12. distillationanhydrous sulfuric acid, and the solvent was distilled off under reduced pressure
  13. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-c5c9fef64a7d43faaed8eb5b9db841aa
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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