Sodium Hydroxide → 2-(4-Chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazole

HRID 1896781

Reaktionsgleichung

Reaktionsgleichung von HRID 1896781
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([S:17][CH3:18])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:24].[OH-:30].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]3[CH:16]=[C:15]([S:17]([CH3:18])(=[O:24])=[O:30])[CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 576174822-(4-Chlorophenyl)-6-(methylthio)benzo[d]thiazole

Produkt 1

HCID 673329402-(4-Chlorophenyl)-6-(methylsulfonyl)benzo[d]thiazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-chlorophenyl)-6-(methylthio)benzo[d]thiazole (240 mg, 0.82 mmol) in dichloromethane (20 mL) was added 3-chloroperoxybenzoic acid (77% in water, 710 mg, 4.11 mmol) over 5 min. The resulting mixture was stirred at room temperature for 3 h. 1M aqueous sodium hydroxide solution was added carefully, and the mixture was then stirred for 5 min. The organic layer was then washed with 1M aqueous sodium hydroxide solution, dried over anhydrous MgSO4 and evaporated. The resulting solid was recrystallised from hot ethyl acetate to afford 125 mg (47%) of the title compound (LCMS RT=6.81 min, MH+ 324.0)

Aufarbeitung

  1. stirringthe mixture was then stirred for 5 min
  2. washThe organic layer was then washed with 1M aqueous sodium hydroxide solution
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customThe resulting solid was recrystallised from hot ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b4c584f9d3f84788a2b0e7e4518ba0cd
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518980B2

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