Acetic Acid → HCID 86625169, compound

HRID 2094819Notes

Reaction equation

HRID 2094819 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2].[S:24]1[CH2:28][C:27](=[O:29])[NH:26][C:25]1=[O:30].C(O)(=O)C.N1CCCCC1>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([S:20]([CH3:23])(=[O:22])=[O:21])[CH2:10][O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=[C:28]3[S:24][C:25](=[O:30])[NH:26][C:27]3=[O:29])=[CH:14][CH:13]=2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 73505385HCID 73505385, compound

Product 1

HCID 86625169HCID 86625169, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

To a stirred solution of 0.65 g (0.0018 mol) 4-[2-(5-ethyl-pyridin-2-yl)-2-mesyl-ethoxy]-benzaldehyde dissolved in 10 mL toluene was added 0.211 g (0.0018 mol) thiazolidin-2,4-dione followed by addition of 0.161 g (0.03 mol) acetic acid and 0.228 g (0.03 mol) piperidine. Reaction mixture was refluxed at 120-130° C. for 4 hr. After completion of reaction on TLC, subsequent work-up gave the titled product. Yield of the product was 0.24 g (29%). The product obtained was identical to the product obtained in example 69.

Workup

  1. customReaction mixture
  2. customAfter completion of reaction on TLC, subsequent work-up

Sources & evidence

ORD record
ord-fea8eb6996954b30bc6f5451761ee0b3
Source dataset
uspto-grants-2013_05
Patent number
US08445685B2

Reaction notes

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