Acetic Acid → HCID 54551481, compound

HRID 1595504Notes

Reaction equation

HRID 1595504 reaction equation
N1CCCCC1.C(O)(=O)C.[N+:11]([C:14]1[CH:15]=[C:16]([S:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][O:32][C:33]3[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=3)=[CH:26][CH:25]=2)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].[S:41]1[CH2:45][C:44](=[O:46])[NH:43][C:42]1=[O:47]>O.C1(C)C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([S:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][O:32][C:33]3[CH:34]=[CH:35][C:36]([CH:39]=[C:45]4[S:41][C:42](=[O:47])[NH:43][C:44]4=[O:46])=[CH:37][CH:38]=3)=[CH:26][CH:25]=2)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21704983HCID 21704983, compound

Product 1

HCID 54551481HCID 54551481, compoundYield 65.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

0.25 g (2.9 mmole) piperidine, 0.174 g (2.9 mmole) acetic acid, 120 ml toluene, 2.5 g (5.8 mmole) 4-[2-(4-formylphenoxy)ethyl]phenyl 3-nitrobenzenesulfonate and 0.86 g (7.3 mmole) 2,4-thiazolidinedione were refluxed with water separation in a Dean-Stark apparatus. When the reaction mixture was allowed to cool yellow crystals formed. The crystals were collected by filtration and stirred in methanol. Filtration gave 2 g (yield 65.5%) of 5-(4-[2-(4-(3-nitrophenylsulfonyloxy)phenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. temperatureto cool yellow crystals
  2. customformed
  3. filtrationThe crystals were collected by filtration
  4. filtrationFiltration

Sources & evidence

ORD record
ord-63f51f1bfab64911a1d82adcd78708dc
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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