Methanesulfonyl chloride → 5-Mesylamino-3-(quinol-4-ylmethylene)-2-oxindole

HRID 356992

Reaktionsgleichung

Reaktionsgleichung von HRID 356992
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>N1C=CC=CC=1>[S:23]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[CH:15][CH:14]=1)([CH3:26])(=[O:25])=[O:24]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 545367025-Amino-3-(quinol-4-ylmethylene)-2-oxindole

Produkt 1

HCID 676153715-Mesylamino-3-(quinol-4-ylmethylene)-2-oxindoleAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-amino-3-(quinol-4-ylmethylene)-2-oxindole (2.873 g, 10 mmol) in pyridine (10 ml) was added gradually mesylchloride (1.146 g, 10 mmol) at 0°-5° C. under cooling. The reaction mixture was stirred for about 5 h at 0°-5° C. and then for 15 hours at room temperature. The mixture was poured onto an ice-water mixture, the precipitate filtered off, the residue washed thoroughly with water and then chromatographed on silica gel using CHCl3 --MeOH mixtures as eluant. Thus pure title compound was obtained in about 70% yield.

Aufarbeitung

  1. temperatureunder cooling
  2. waitfor 15 hours at room temperature
  3. filtrationthe precipitate filtered off
  4. washthe residue washed thoroughly with water
  5. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ec00d732ae1f4797a0ea72a0b1697788
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840745

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