Sodium Bicarbonate → 5-[(4-Aminophenyl)sulfonyl]thiazole

HRID 2292919

Reaktionsgleichung

Reaktionsgleichung von HRID 2292919
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[S:17][CH:16]=[N:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[S:17][CH:16]=[N:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 107071535-[(4-Nitrophenyl)sulfonyl]thiazole

Produkt 1

HCID 107287585-[(4-Aminophenyl)sulfonyl]thiazoleAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred solution of 5-[(4-nitrophenyl)sulfonyl]thiazole (1.72 g, 6.4 mmol) and stannous chloride dihydrate (7.17 g, 31.8 mmol) in absolute ethanol (25 mL) was heated at reflux for 1 hour. The reaction mixture was poured into ice water, the aqueous solution basified with solid sodium bicarbonate and extracted with ethyl acetate (2×200 mL). The combined organic portions were dried (MgSO4), filtered, and the solvent removed to yield an orange solid. Flash chromatography (eluted with 10% ethyl acetate in methylene chloride) and evaporation of the solvent yielded the title thiazole (1.20 g, 78%) as a pale yellow solid; mp 158°-160° C. 1H-NMR (250 MHz, d6 -DMSO): 6.35 (br s, 2H, NH2), 6.65 (d, 2H, J=8.9 Hz, aromatic), 7.61 (d, 2H, J=8.7 Hz, aromatic), 8.39 (s, 1H, aromatic), 9.38 (s, 1H, aromatic). MS (CI, CH4): 241(M+1).

Aufarbeitung

  1. temperatureat reflux for 1 hour
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialThe combined organic portions were dried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto yield an orange solid
  7. washFlash chromatography (eluted with 10% ethyl acetate in methylene chloride) and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-aef5a34f56e04623a4fd3abfd80ae958
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684198

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