Citric Acid → 3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone

HRID 2224761Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224761
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:23](=[O:24])[C:22]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[OH:31])=O)(=[O:4])=[O:3].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[OH-].[K+]>[O:4]=[S:2]1(=[O:3])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][C:12]([C:14]2[C:23](=[O:24])[C:22]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[C:21]3[C:16]([C:15]=2[OH:31])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:1]1

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 54723969N-[2-(aminosulfonyl)phenyl]-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxamide

Produkt 1

HCID 1355144473-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenoneAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14797Potassium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A suspension of the product of Example 1G (150 mg, 0.34 mmol) in 10% potassium hydroxide solution (9 mL) was stirred at 130° C. for 30 hours, cooled to 25° C., acidified to pH 3 by addition of 1 M citric acid, stirred with ethyl acetate, and filtered through celite®. The organic layer from the filtrate was washed with saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo. The residue was recrystallized from ether-hexane solution to afford the title compound (83 mg, 57%). 1H NMR (300 MHz, CDCl3): δ16.70 (s, 1 H), 14.22 (s, 1 H), 8.26 (d, J=8.09 Hz, 1 H), 7.99 (d, J=8.09 Hz, 1 H), 7.67 (m, 1 H), 7.47 (m, 3 H), 7.29 (m, 2 H), 2.25 (m, 2 H), 1.86 (m, 2 H), 0.89 (m, 2 H), 0.70 (m, 8 H).

Aufarbeitung

  1. temperaturecooled to 25° C.
  2. filtrationfiltered through celite®
  3. washThe organic layer from the filtrate was washed with saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ether-hexane solution

Quellen und Nachweise

ORD-Eintrag
ord-abf0edc3648e43db8f1eced0db3e57f6
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378414B2

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