5-(2-Chlorophenyl)furfural → HCID 86644300, Verbindung

HRID 2197681

Reaktionsgleichung

Reaktionsgleichung von HRID 2197681
[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].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[O:29][C:28]([CH:30]=O)=[CH:27][CH:26]=1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[O:29][C:28]([CH:30]=[C:6]2[S:5][C:4](=[S:7])[N:3]([NH:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11]([OH:13])=[O:12])[C:2]2=[O:1])=[CH:27][CH:26]=1

Komponenten

6

Edukt 4

HCID 6098215-(2-Chlorophenyl)furfuralHCID 4594337HCID 4594337, VerbindungHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

Produkt 1

HCID 86644300HCID 86644300, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.090 g, 0.34 mmol), 5-(2-chloro-phenyl)-furan-2-carbaldehyde (0.074 g, 0.36 mmol) (purchased from Aldrich Chemical Co.) and ethylenediamine diacetate (0.065 g, 0.036 mmol) in methanol (8 mL) was stirred at room temperature for 17 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 15 min. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (2 mL), water (2×2 mL), ether (2 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 19 h to afford 2-{5-[1-[5-(2-Chloro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (141 mg, 92%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.55 (1H, d, J=8.0 Hz), 6.87 (1H, t, J=7.6 Hz), 7.32 (1H, t, J=7.6 Hz), 7.44-7.51 (3H, m), 7.62 (1H, d, J=8.0 Hz), 7.66 (1H, d, J=8.4 Hz), 7.80 (1H, s), 7.91 (1H, d, J=8.0 Hz), 7.97 (1H, d, J=8.0 Hz). LC/MS: APCI 457.2, HPLC 97.9%

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 15 min
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with 0.6 N aq sodium hydrogensulfite (2 mL), water (2×2 mL), ether (2 mL) and hexanes (2 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 19 h

Quellen und Nachweise

ORD-Eintrag
ord-8f1d28d31b87457bb8846e1a576c1406
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338465B2

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