Benzoic Acid → HCID 54132072, compound

HRID 2119925Notes

Reaction equation

HRID 2119925 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[S:29]1[CH2:33][C:32](=[O:34])[NH:31][C:30]1=[O:35].N1CCCCC1.C(O)(=O)C1C=CC=CC=1>C1(C)C=CC=CC=1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:33]2[S:29][C:30](=[O:35])[NH:31][C:32]2=[O:34])=[CH:23][CH:22]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 10068863HCID 10068863, compound

Product 1

HCID 54132072HCID 54132072, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-(2-(N-(2-Benzothiazolyl)-N-benzylamino)ethoxy)benzaldehyde (3 g) and 2,4-thiazolidinedione (1 g) were dissolved in toluene (200 ml) containing piperidine (0.2 ml) and benzoic acid (0.2 g) and heated to reflux for 4 h. in a Dean and Stark apparatus. On cooling, the solution was concentrated under vacuum to 50% of its volume and the title compound, which crystallised, was collected by filtration and dried in vacuo (m.p. 185-188° C.). It was used in Example 27 without further purification.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h. in a Dean and Stark apparatus
  3. temperatureOn cooling
  4. concentrationthe solution was concentrated under vacuum to 50% of its volume
  5. customthe title compound, which crystallised
  6. filtrationwas collected by filtration
  7. customdried in vacuo (m.p. 185-188° C.)
  8. customIt was used in Example 27 without further purification

Sources & evidence

ORD record
ord-fcc0d8c77f264652ae46743ffb7b9c2b
Source dataset
uspto-grants-2004_02
Patent number
US06686475B2

Reaction notes

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