5-(3-(Trifluoromethyl)phenyl)furfural → HCID 86644302, compound

HRID 2197685

Reaction equation

HRID 2197685 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].[F:18][C:19]([F:34])([F:33])[C:20]1[CH:21]=[C:22]([C:26]2[O:30][C:29]([CH:31]=O)=[CH:28][CH:27]=2)[CH:23]=[CH:24][CH:25]=1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[O:1]=[C:2]1[C:6](=[CH:31][C:29]2[O:30][C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([C:19]([F:33])([F:18])[F:34])[CH:21]=3)=[CH:27][CH:28]=2)[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]

Participants

6

Reactant 4

HCID 7218375-(3-(Trifluoromethyl)phenyl)furfuralHCID 4594337HCID 4594337, compoundHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium Bisulfite

Product 1

HCID 86644302HCID 86644302, compoundYield 79%

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-(3-trifluoromethyl-phenyl)-furan-2-carbaldehyde (0.086 g, 0.36 mmol) (purchased from Aldrich Chemical Company) 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 mm. 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-{4-Oxo-2-thioxo-5-[1-[5-(3-trifluoromethyl-phenyl)-furan-2-yl]-methylidene]-thiazolidin-3-ylamino}-benzoic acid (130 mg, 79%) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 6.53 (1H, m), 6.86 (1H, m), 7.29 (1H, m), 7.43 (1H, d, J=3.6 Hz), 7.59 (1H, d, J=3.6 Hz), 7.78 (1H, s), 7.82 (2H, m), 7.92 (1H, m), 8.16 (1H, m), 8.21 (1H, m). LC/MS: APCI 489.3, HPLC 97.1%

Workup

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 15 mm
  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-ba19cf6761d3480ab16ffcf3da0d1504
Source dataset
uspto-grants-2012_12
Patent number
US08338465B2

Linked notes

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