2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid → 2-{5-[1-[5-(4-Morpholin-4-yl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197687

Reaktionsgleichung

Reaktionsgleichung von HRID 2197687
[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].[N:18]1([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[O:34][C:33]([CH:35]=O)=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[N:18]1([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[O:34][C:33](/[CH:35]=[C:6]4\[C:2](=[O:1])[N:3]([NH:8][C:9]5[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=5[C:11]([OH:13])=[O:12])[C:4](=[S:7])[S:5]\4)=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Komponenten

6

Edukt 4

HCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acidHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium BisulfiteHCID 594462295-(4-Morpholin-4-yl-phenyl)-furan-2-carbaldehyde

Produkt 1

HCID 247757292-{5-[1-[5-(4-Morpholin-4-yl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acidAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.089 g, 0.33 mmol), 5-(4-morpholin-4-yl-phenyl)-furan-2-carbaldehyde (0.091 g, 0.35 mmol) and ethylenediamine diacetate (0.063 g, 0.035 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 mm. 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-(4-morpholin-4-yl-phenyl)-furan-2-yl]-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (147 mg, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6): 3.26 (2H, m), 3.76 (2H, m), 6.53 (1H, d, J=8.4 Hz), 6.87 (1H, m), 7.14 (2H, m), 7.17 (1H, d, J=3.6 Hz), 7.31 (1H, m), 7.40 (1H, d, J=4.0 Hz), 7.71 (1H, s), 7.76 (2H, m), 7.91 (1H, m), 10.4 (1H, bs). LC/MS: APCI 506.1, HPLC 92%.

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 30 mm
  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-0d282683e76540f7a65adc92a75b9e32
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338465B2

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