Water → HCID 21845561, Verbindung

HRID 619069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 619069
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[S:17][CH:18]=2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10].O.[CH3:31]N(C)C=O>>[OH:3][C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([NH:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[S:17][CH:18]=2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:10][CH3:31]

Komponenten

5

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 21845565HCID 21845565, Verbindung

Produkt 1

HCID 21845561HCID 21845561, Verbindung

Versuchsvorschrift

50 mg of sodium hydride (60%) were added to a solution of 0.5 g of N-[4-(3,4-dihydroxy-5-nitro-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide in 5 ml of dimethylformamide. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The organic phase was dried with magnesium sulphate and concentrated. The residue was chromatographed on 60 g of Kieselgel 60 with methylene chloride/acetone/formic acid (90:10:2.5) as the eluent. The product-containing fractions were concentrated and, after boiling with 20 ml of diethyl ether, yielded 0.17 g of N-[4-(3-hydroxy-4-methoxy-5-nitro-phenyl)-thiazol-2-yl]-4-methyl-benzenesulfonamide as orange colored crystals.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. concentrationconcentrated
  4. customThe residue was chromatographed on 60 g of Kieselgel 60 with methylene chloride/acetone/formic acid (90:10:2.5) as the eluent
  5. concentrationThe product-containing fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7dbf44d9d00048ac941f24bd8d0d2b51
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05958910

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