Benzoic Acid → (E)-Methyl 4-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)ethoxy)benzoate

HRID 852964Notes

Reaction equation

HRID 852964 reaction equation
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][O:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)=O.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[O:29]=[C:24]1[NH:25][C:26](=[O:28])/[C:27](=[CH:1]\[C:3]2[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][O:10][C:11]3[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:5][CH:4]=2)/[S:23]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 18526174Methyl 4-(2-(4-formylphenoxy)ethoxy)benzoate

Product 1

HCID 58930528(E)-Methyl 4-(2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)ethoxy)benzoateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 355 (1.59 g, 3.86 mmol) in toluene (10 mL) was added thiazolidine-2,4-dione (542 mg, 4.63 mmol), benzoic acid (61.3 mg, 0.50 mmol) and piperidine (57 μL, 0.58 mmol). The resultant mixture was refluxed with the Dean-Stark adapter for ½ h and cooled to the room temperature. A precipitate formed which was collected by filtration to afford the title compound (1.41 g, 92%). 1H NMR: (DMSO-d6) δ (ppm): 7.90 (d, J=8.8 Hz, 2H), 7.73 (s, 1H), 7.54 (d, J=8.8 Hz, 2H), 7.14 (d, J=8.8 Hz, 2H), 7.08 (d J=8.8 Hz, 2H), 4.42 (bs, 4H), 3.80 (s, 3H). LRMS (ESI): (calc.) 399.1; (found) 400.0 (MH)+.

Workup

  1. customA precipitate formed which
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d473aba8345f4a5d8d83811d09ae2574
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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