Dimethylformamide → 3-Ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione

HRID 30644

Reaction equation

HRID 30644 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[S:13][C:12](=[O:14])[NH:11][C:10]2=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].CN(C)C=O.[H-].[Na+].I[CH2:26][CH3:27]>O>[CH2:26]([N:11]1[C:10](=[O:15])[C:9](=[CH:8][C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[S:13][C:12]1=[O:14])[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27682645-(4-Nitrobenzylidene)-1,3-thiazolidine-2,4-dione

Product 1

HCID 47605383-Ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dioneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione (3.50 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60% in oil, 0.62 g) at room temperature. The reaction mixture was stirred at room temperature for 30 min. and iodoethane (6.55 g) was added to the reaction mixture. The mixture was stirred at room temperature for 15 hrs. Water was added to the reaction mixture and the precipitated crystals were collected by filtration to give 3-ethyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione as yellow crystals (3.81 g, yield 98%). Recrystallization thereof from acetone-hexane gave yellow prism crystals. melting point: 217-218° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 15 hrs
  2. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-9060992ab9a0418c9aa58597578f281b
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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