HCID 4594337, compound → 2-{5-[1-[5-(4-Tert-butyl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197683

Reaction equation

HRID 2197683 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].[C:18]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:32][C:31]([CH:33]=O)=[CH:30][CH:29]=2)=[CH:24][CH:23]=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:27]=[CH:26][C:25]([C:28]2[O:32][C:31](/[CH:33]=[C:6]3\[C:2](=[O:1])[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:4](=[S:7])[S:5]\3)=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 4594337HCID 4594337, compoundHCID 10154317Ethylenediamine diacetateHCID 22566716HCID 22566716, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 247757252-{5-[1-[5-(4-Tert-butyl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.090 g, 0.34 mmol), 5-(4-tert-butyl-phenyl)-furan-2-carbaldehyde (0.082 g, 0.36 mmol) 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-(4-tert-Butyl-phenyl)-furan-2-yl]-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (140 mg, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 1.32 (9H, s), 6.45 (1H, m), 6.82 (1H, m), 7.23 (1H, m), 7.30 (1H, d, J=3.6), 7.40 (1H, d, J=3.6), 7.61 (2H, m), 7.74 (1H, s), 7.82 (2H, m), 7.91 (1H, m), 11.20 (1H, bs). LC/MS APCI 477.9, HPLC 91.0%

Workup

  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

Sources & evidence

ORD record
ord-0666dfb1d4304484be56ae3659c14898
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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