Benzoic Acid → 5-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzylidene)-2,4-thiazolidinedione

HRID 2260716Notes

Reaction equation

HRID 2260716 reaction equation
[C:1]([N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:22]1[CH2:26][C:25](=[O:27])[NH:24][C:23]1=[O:28].C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[C:1]([N:9]([CH2:11][CH2:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[C:26]2[S:22][C:23](=[O:28])[NH:24][C:25]2=[O:27])=[CH:16][CH:15]=1)[CH3:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 189988924-[2-(N-Benzoyl-N-methylamino)ethoxy]benzaldehyde

Product 1

HCID 545522965-(4-[2-(N-Benzoyl-N-methylamino)ethoxy]benzylidene)-2,4-thiazolidinedione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-[2-(N-benzoyl-N-methylamino)ethoxy]benzaldehyde (3.94 g), 2,4-thiazolidinedione (1.79 g), benzoic acid (0.2 g) and piperidine (0.2 ml) were heated at reflux in toluene (250 ml) in a Dean and Stark apparatus. After 5 hours at reflux the mixture was allowed to cool and crystallise overnight. The title compound, mp 178-180° C., was filtered off, washed with cold toluene and dried under vacuum.

Workup

  1. temperaturewere heated
  2. temperatureAfter 5 hours at reflux the mixture
  3. temperatureto cool
  4. customcrystallise overnight
  5. filtrationThe title compound, mp 178-180° C., was filtered off
  6. washwashed with cold toluene
  7. customdried under vacuum

Sources & evidence

ORD record
ord-a64358baef184d3998b3fda19dd189a7
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

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