HCID 12093195, Verbindung → (2,7-bis{[(3-Hydroxyphenyl)amino]sulfonyl}-9H-fluoren-9-ylidene)acetic Acid

HRID 2120915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2120915
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:27])=[O:26])=[CH:19][CH:20]=4)[C:15](=[CH:36][C:37]([O:39]CC)=[O:38])[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1>C1COCC1.[OH-].[Na+]>[OH:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:26])=[O:27])=[CH:19][CH:20]=4)[C:15](=[CH:36][C:37]([OH:39])=[O:38])[C:14]=3[CH:13]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 12093195HCID 12093195, Verbindung

Produkt 1

HCID 10053631(2,7-bis{[(3-Hydroxyphenyl)amino]sulfonyl}-9H-fluoren-9-ylidene)acetic AcidAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

The product from Example 5A (460 mg, 0.78 mmol) in THF (5 mL) and 15% aqueous NaOH (5 mL) was heated at reflux for 6 hours. The mixture was allowed to cool to ambient temperature, acidified, and extracted with ethyl acetate. The organic phase was separated, washed with brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide the title compound as a yellow solid (95 mg, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 10.16 (s, 1H), 9.43 (s, 1H), 9.18 (d, 1H), 8.37 (d, 1H), 8.1 (m, 2H), 7.86 (m, 2H), 7.2 (s, 1H), 7.0 (t, 2H), 6.53-6.63(m, 4H), 6.42 (m, 2H). MS (ESI) 563 (M−H)−.

Aufarbeitung

  1. temperatureat reflux for 6 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4124d2fabaad40c6bc36e3428eece037
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06693136B1

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