Toluene → HCID 86591247, compound

HRID 584891Notes

Reaction equation

HRID 584891 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:25])[C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:10]=2)=[CH:5][CH:4]=1)=O.[S:26]1[CH2:30][C:29](=[O:31])[NH:28][C:27]1=[O:32].C(O)(=O)C.N1CCCCC1.C1(C)C=CC=CC=1>O>[O:32]=[C:27]1[NH:28][C:29](=[O:31])[C:30](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([CH3:25])[C:17](=[O:24])[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:10]=3)=[CH:7][CH:8]=2)[S:26]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 9793820Piperidine, acetateHCID 22341491N-(4'-formylbiphenyl-3-ylmethyl)-N-methylbenzamide

Product 1

HCID 86591247HCID 86591247, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.6 g (4.6 mmol) of N-(4′-Formylbiphenyl-3-ylmethyl)-N-methylbenzamide, 610 mg (4.6 mmol) of 2,4-thiazolidine dione, 137 mg of piperidine acetate and 60 ml of toluene are introduced into a round-bottomed flask under a stream of nitrogen. The mixture is refluxed for five hours and the water formed is separated out using Dean-Stark apparatus. The reaction medium is cooled and the precipitate formed is filtered off and purified on a column of silica with an fluent mixture of heptane and ethyl acetate (70/30). After evaporation of the solvents, 1.4 g (70%) of the expected product are collected.

Workup

  1. temperatureThe mixture is refluxed for five hours
  2. customis separated out
  3. temperatureThe reaction medium is cooled
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. custompurified on a column of silica with an fluent mixture of heptane and ethyl acetate (70/30)
  7. customAfter evaporation of the solvents, 1.4 g (70%) of the expected product
  8. customare collected

Sources & evidence

ORD record
ord-a966f4dae6e843f4aebf9d11b785559c
Source dataset
uspto-grants-2005_08
Patent number
US06927228B2

Reaction notes

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