Acetic Acid → HCID 73989463, compound

HRID 1816579Notes

Reaction equation

HRID 1816579 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=1)[CH2:8][NH:9][C:10](=[O:21])[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=O.[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[O:31]=[C:26]1[NH:27][C:28](=[O:30])[C:29](=[CH:1][C:3]2[CH:4]=[CH:5][C:6]([O:23][CH3:24])=[C:7]([CH:22]=2)[CH2:8][NH:9][C:10](=[O:21])[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[S:25]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5437ThiazolidinedioneHCID 31268PyrrolidineHCID 22494151HCID 22494151, compound

Product 1

HCID 73989463HCID 73989463, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.5 g of N1-(5-formyl-2-methoxybenzyl)-4-(trifluoromethyl)benzamide was dissolved in 15 ml toluene, and 0.52 g of 2,4-thiazolidine dione, 36 mg pyrrolidine and 30 mg acetic acid were added thereto, and the mixture was heated under reflux for 2 hours with a Dean-Stark apparatus. After cooling to room temperature, the precipitated crystals were collected by filtration, washed with ethyl acetate and then dried, to give 1.4 g of N1-[5-[(2,4-dioxo-1,3-thiazolane-5-ylidene)methyl]-2-methoxybenzyl)-4-(trifluoromethyl)benzamide.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours with a Dean-Stark apparatus
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-c267498664f947a981c3cbe58dfbb577
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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