3H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl- → 4-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1289823
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]([CH3:8])=[N:3]1.[F-].[K+].Cl[CH2:12][N:13]1[C:17](=[O:18])[C:16]2[C:19]([CH:25]([CH3:27])[CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=2[S:14]1(=[O:29])=[O:28]>CN(C=O)C>[CH:25]([C:19]1[C:16]2[C:17](=[O:18])[N:13]([CH2:12][O:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:8])[CH:5]=3)[S:14](=[O:29])(=[O:28])[C:15]=2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=1)([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 176733H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl-HCID 522689Potassium FluorideHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

Produkt 1

HCID 189225454-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxideAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,4-dihydro-2,5-dimethyl-3H-pyrazol-3-one (475 mg; 4.24 mmol) in DMF (25 ml) was added 280 mg (4.83 mmol) of KF followed by 2-chloromethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1 g, 3.3 mmol), and the resulting mixture was stirred at room temperature for 24 hours and then was poured into ice/water. The above mixture was extracted with ethyl acetate and the organic layer was washed with water, dried, and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.46 g (37%) of 4-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =R2 =CH3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 146°-147° C.

Aufarbeitung

  1. extractionThe above mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0325d04e602d45639edf762f2127e922
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05750550

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