Water → HCID 86601583, compound

HRID 1172084Notes

Reaction equation

HRID 1172084 reaction equation
Cl.[CH3:2][O:3][NH2:4].C([O-])(=O)C.[Na+].[C:10]([C:13]1[C:14]([CH2:20][S:21][C:22]2[CH2:26][C:25]([CH3:28])([CH3:27])[O:24][N:23]=2)=[C:15]([CH3:19])[S:16][C:17]=1[CH3:18])(=O)[CH3:11].O>C(O)C>[CH3:27][C:25]1([CH3:28])[O:24][N:23]=[C:22]([S:21][CH2:20][C:14]2[C:13]([C:10](=[N:4][O:3][CH3:2])[CH3:11])=[C:17]([CH3:18])[S:16][C:15]=2[CH3:19])[CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 17862880HCID 17862880, compound

Product 1

HCID 86601583HCID 86601583, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.57 g (6.8 mmoles) of O-methylhydroxylamine hydrochloride and 0.56 g (6.8 mmoles) of sodium acetate were added to a solution of 1.0 g (3.4 mmoles) of 3-(4-acetyl-2,5-dimethylthiophen-3-ylmethylthio)-5,5-dimethyl-2-isoxazoline dissolved in 50 ml of ethanol. The mixture was stirred for 5 hours under refluxing, to give rise to a reaction. After confirmation of the completion of the reaction, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent) to obtain 0.4 g (36.4%) of 5,5-dimethyl-3-[2,5-dimethyl-4-(1-methoxyiminoethyl)-thiophen-3-ylmethylthio]-2-isoxazoline as a yellow oily substance.

Workup

  1. temperatureunder refluxing
  2. customto give rise
  3. customto a reaction
  4. customAfter confirmation of the completion of the reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with water
  7. dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
  8. distillationThe resulting solution was subjected to vacuum distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate mixed solvent)

Sources & evidence

ORD record
ord-c50acc3ff0a34739ab41cbba15be310c
Source dataset
uspto-grants-2010_11
Patent number
US07833939B2

Reaction notes

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