Water → [(5-Chloro-3-methyl-isothiazol-4-yl)-methylsulfonyl]-5,5-dimethyl-2-isoxazoline

HRID 1172083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172083
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[S:17][N:16]=[C:15]([CH3:18])[C:14]=1[CH2:19][S:20][C:21]1[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][N:22]=1.[OH2:28]>C(Cl)(Cl)Cl>[Cl:12][C:13]1[S:17][N:16]=[C:15]([CH3:18])[C:14]=1[CH2:19][S:20]([C:21]1[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][N:22]=1)(=[O:9])=[O:28]

Komponenten

5

Edukt 3

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 17862903[(5-Chloro-3-methyl-isothiazol-4-yl)methylthio]-5,5-dimethyl-2-isoxazoline

Produkt 1

HCID 17862869[(5-Chloro-3-methyl-isothiazol-4-yl)-methylsulfonyl]-5,5-dimethyl-2-isoxazolineAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

2.96 g of m-chloroperbenzoic acid (purity: 70%, 12.00 mmoles) was added, with ice-cooling, to a solution of 1.38 g (5.00 mmoles) of [(5-chloro-3-methyl-isothiazol-4-yl)-methylthio]-5,5-dimethyl-2-isoxazoline dissolved in 20 ml of chloroform. The mixture was stirred for 1 hour and then at room temperature for overnight to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into water, followed by extraction with chloroform. The resulting organic layer was washed with an aqueous sodium hydrogensulfite solution, an aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The reside was purified by silica gel column chromatography to obtain 0.65 g (yield: 47.0%) of [(5-chloro-3-methyl-isothiazol-4-yl)-methylsulfonyl]-5,5-dimethyl-2-isoxazoline as a light yellow powder (melting point: 113 to 114° C.).

Aufarbeitung

  1. customat room temperature for overnight to give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. extractionfollowed by extraction with chloroform
  5. washThe resulting organic layer was washed with an aqueous sodium hydrogensulfite solution
  6. dry with materialan aqueous sodium hydrogencarbonate solution and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  7. distillationThe resulting solution was subjected to vacuum distillation
  8. customto remove the solvent
  9. customThe reside was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a9cc98320bfd4cfb804c7e98f05c4e02
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833939B2

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