Water → 7-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedione

HRID 2301293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301293
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[NH:13][C:12]1=[O:23])(=[O:10])=[O:9].[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>N1C=CC=CC=1>[Cl:22][C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([S:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][S:25]([CH3:24])(=[O:27])=[O:26])(=[O:10])=[O:9])[C:12](=[O:23])[NH:13]2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 98413923-(2-Aminobenzenesulfonyl)-7-Chloro-2,4(1H,3H)-Quinazolinedione

Produkt 1

HCID 98673267-chloro-3-(2-methylsulfonylaminobenzenesulfonyl)-2,4(1H,3H)-quinazolinedioneAusbeute 66,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

22 mg (0.06 mmol) of Compound 2 was dissolved in 200 μl of pyridine, 11.6 μl (0.15 mmol) of methanesulfonyl chloride was added dropwise, then the resultant mixture was stirred at room temperature overnight. An excess amount of water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline, then dried over anhydrous magnesium sulfate and concentrated to obtain a crude product. The crude product was crystallized from diethyl ether to obtain 16 mg (0.04 mmol) of the above-identified compound. Properties: colorless crystal, Melting point: >200° C. (decomposition), PMR (δ ppm, DMSO-d6): 3.61 (3H, s), 7.10 (1H, d), 7.20 (1H, d), 7.74 (1H, d), 7.82-7.90 (4H, m), 8.34 (1H, d), 11.70 (1H, s).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N aqueous hydrochloric acid solution and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto obtain a crude product
  6. customThe crude product was crystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-45b8741254a24b13bb639c878acb4d03
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500835B2

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