Acetic Acid → HCID 54012500, compound

HRID 1595521Notes

Reaction equation

HRID 1595521 reaction equation
[CH:1]([C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:20])[O:18][CH3:19])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)=O.[S:23]1[CH2:27][C:26](=[O:28])[NH:25][C:24]1=[O:29].N1CCCCC1.C(O)(=O)C>O.C1(C)C=CC=CC=1>[CH3:19][O:18][C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][O:7][C:6]2[CH:21]=[CH:22][C:3]([CH:1]=[C:27]3[S:23][C:24](=[O:29])[NH:25][C:26]3=[O:28])=[CH:4][CH:5]=2)=[CH:11][CH:12]=1)=[O:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 21705020HCID 21705020, compound

Product 1

HCID 54012500HCID 54012500, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

2 g (6.7 mmole) methyl N-{4-[2-(4-formylphenoxy)ethyl]phenyl}carbamate, 1.57 g (13.4 mmole) 2,4-thiazolidinedione, piperidine, acetic acid and toluene were refluxed with water separation in a Dean-Stark apparatus for 3 hours. The formed yellow precipitate was collected by filtration giving 1.9 g (yield 71.2%) of 5-(4-[2-(4-methoxycarbonylaminophenyl)ethoxy]benzylidene)thiazolidine-2,4-dione.

Workup

  1. filtrationThe formed yellow precipitate was collected by filtration

Sources & evidence

ORD record
ord-e47c9648506e47f28ed179e19fb3a9f9
Source dataset
uspto-grants-2001_09
Patent number
US06288096B1

Reaction notes

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