HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzoic Acid → 2-{4-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid

HRID 2217622
Notes
Print preview

Reaction equation

HRID 2217622 reaction equation
[CH:1]([C:3]1[CH:27]=[CH:26][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14](=[CH:18][C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)=O.[S:28]1[CH2:32][C:31](=[O:33])[NH:30][C:29]1=[O:34].C(O)(=O)C1C=CC=CC=1.N1CCCCC1.Cl>C1(C)C=CC=CC=1>[O:34]=[C:29]1[NH:30][C:31](=[O:33])[C:32](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([O:7][C:8]3[CH:9]=[CH:10][C:11]([C:14](=[CH:18][C:19]4[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=4)[C:15]([OH:17])=[O:16])=[CH:12][CH:13]=3)=[CH:26][CH:27]=2)[S:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 243Benzoic AcidHCID 313Hydrochloric AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 725565312-[4-(4-Formylphenoxy)-phenyl]-3-p-tolylacrylic acid

Product 1

HCID 725565302-{4-[4-(2,4-Dioxothiazolidin-5-ylidenemethyl)-phenoxy]-phenyl}-3-p-tolylacrylic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 39 (4.0 g, 11.2 mmol), thiazolidine-2,4-dione (1.31 g, 11.2 mmol), and benzoic acid (1.64 g, 13.4 mmol) in 100 mL toluene was added piperidine (1.66 mL, 16.8 mmol). The mixture was vigorously refluxed with Dean Stark apparatus for 1.5 h under argon then cooled to room temperature. 5% HCl was added to pH 1. The solid was filtered, recrystallized out of toluene, filtered, and washed with hexane before drying under vacuum to a yellow solid (quantitative). 1H NMR (400 MHz, DMSO-d6) δ 12.70 (br s, 1H), 12.59 (br s, 1H), 7.80 (s, 1H), 7.75 (s, 1H), 7.67 (d, J=8.8 Hz, 2H), 7.22 (d, J=9.2 Hz, 2H), 7.18 (d, J=7.6 Hz, 2H), 7.12 (d, J=9.2 Hz, 2H), 7.07 (d, J=8.0 Hz, 2H), 6.99 (d, J=8.0 Hz, 2H), 2.25 (s, 3H).

Workup

  1. temperatureThe mixture was vigorously refluxed with Dean Stark apparatus for 1.5 h under argon
  2. filtrationThe solid was filtered
  3. customrecrystallized out of toluene
  4. filtrationfiltered
  5. washwashed with hexane
  6. custombefore drying under vacuum to a yellow solid (quantitative)

Sources & evidence

ORD record
ord-68539a230cfa408fbde1937b673a9502
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07407978B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes