Dichloromethane → Methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

HRID 2167426Notes

Reaction equation

HRID 2167426 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[N:13][OH:14])=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:20]Cl.[C:22]([O-])(=O)[CH3:23].[Na+].Cl[O-].[Na+]>C=CC>[Cl:1][C:2]1[C:11]([C:12]2[CH2:20][CH:22]([CH3:23])[O:14][N:13]=2)=[C:10]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 23665760Sodium HypochloriteHCID 86584467Methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate

Product 1

HCID 22114913Methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate

Reagents, catalysts & solvents 1

HCID 8252PropyleneSolvent4×

Procedure

Propene was passed for 30 minutes at room temperature into a solution of 15.0 g (52 mmol) of methyl 2-chloro-3-hydroxyiminomethyl-4-methylsulfonylbenzoate and 200 ml of dichloromethane. After 1.6 g of sodium acetate had been added, 42.8 ml of sodium hypochlorite solution were added dropwise at room temperature while simultaneously passing in propene. Propene was subsequently passed in for a further 15 minutes at room temperature. After the mixture had been refluxed for 3 hours, it was stirred for 12 hours at room temperature, propene was again passed in for 5 hours under reflux, and the mixture was stirred for a further 12 hours at room temperature. After the phases had been separated, the organic phase was washed with water, dried and concentrated. This gave 15.5 g (89% of theory) of methyl 2-chloro-(5-methyl-4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoate.

Workup

  1. customwas subsequently passed in for a further 15 minutes at room temperature
  2. temperatureAfter the mixture had been refluxed for 3 hours
  3. customwas again passed in for 5 hours
  4. temperatureunder reflux
  5. stirringthe mixture was stirred for a further 12 hours at room temperature
  6. customAfter the phases had been separated
  7. washthe organic phase was washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c1f9f85384f445a3ab52a78b138721b4
Source dataset
uspto-grants-2015_06
Patent number
US09045465B1

Reaction notes

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