HCID 4594337, Verbindung → 2-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197680

Reaktionsgleichung

Reaktionsgleichung von HRID 2197680
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[C:18]([C:22]1[CH:23]=[CH:24][C:25]([OH:35])=[C:26]([C:28]2[O:32][C:31]([CH:33]=O)=[CH:30][CH:29]=2)[CH:27]=1)([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([OH:35])=[C:26]([C:28]2[O:32][C:31]([CH:33]=[C:6]3[S:5][C:4](=[S:7])[N:3]([NH:8][C:9]4[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=4[C:11]([OH:13])=[O:12])[C:2]3=[O:1])=[CH:30][CH:29]=2)[CH:27]=1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

6

Edukt 4

HCID 4594337HCID 4594337, VerbindungHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium BisulfiteHCID 594462335-(5-Tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde

Produkt 1

HCID 866442992-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acidAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.078 g, 0.29 mmol), 5-(5-tert-butyl-2-hydroxy-phenyl)-furan-2-carbaldehyde and (0.075 g, 0.31 mmol) and ethylenediamine diacetate (0.056 g, 0.031 mmol) in methanol (10 mL) was stirred at room temperature for 18 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 30 min. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(5-tert-Butyl-2-hydroxy-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (135 mg, 94%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.37 (9H, s), 6.98 (1H, d, J=8.4 Hz), 7.23 (1H, d, J=3.6 Hz), 7.34 (1H, dd, J=8.8, 2.8 Hz), 7.39 (1H, d, J=3.6 Hz), 7.70 (2H, m), 7.74 (1H, s), 7.94 (1H, d, J=2.4 Hz), 8.01 (1H, m), 8.07 (1H, m). LC/MS. APCI 493.1, HPLC 100%.

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 30 min
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 17 h

Quellen und Nachweise

ORD-Eintrag
ord-10ae44409558468b9c13a01ac7f714eb
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338465B2

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