5-(3-Nitrophenyl)furfural → 2-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197684

Reaction equation

HRID 2197684 reaction equation
[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]([C:21]1[CH:22]=[C:23]([C:27]2[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19].C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[N+:18]([C:21]1[CH:22]=[C:23]([C:27]2[O:31][C:30]([CH:32]=[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:29][CH:28]=2)[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 6124175-(3-Nitrophenyl)furfuralHCID 4594337HCID 4594337, compoundHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

Product 1

HCID 866443012-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acidYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.092 g, 0.34 mmol), 5-(3-nitrophenyl)furan-2-carbaldehyde (0.071 g, 0.33 mmol) (purchased from Aldrich Chemical Company) and ethylenediamine diacetate (0.059 g, 0.033 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), acetonitrile (1 mL), ether (2×2 mL) and acetonitrile (1 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(3-Nitro-phenyl)-furan-2-yl]-methylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (115 mg, 72%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.62 (1H, m), 6.90 (1H, m), 7.37 (1H, m), 7.44 (1H, d, J=3.6 Hz), 7.64 (1H, d, J=3.6 Hz), 7.80 (1H, s), 7.88 (1H, m), 7.92 (1H, m), 8.28 (2H, m), 8.65 (1H, m), 10.2 (1H, bs). LC/MS: APCI 466.7, HPLC 96.5%

Workup

  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), acetonitrile (1 mL), ether (2×2 mL) and acetonitrile (1 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 17 h

Sources & evidence

ORD record
ord-a03c62b184944d779ad22ecd95ee0a6e
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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