Dimethylformamide → 3-Methyl-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione

HRID 30643

Reaction equation

HRID 30643 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].[CH3:18]N(C)C=O.[H-].[Na+].IC>O>[CH3:18][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]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27682645-(4-Nitrobenzylidene)-1,3-thiazolidine-2,4-dione

Product 1

HCID 14828843-Methyl-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione (4.0 g) and N,N-dimethylformamide (100 mL) was added sodium hydride (60% in oil, 0.7 g) at room temperature. The reaction mixture was stirred at room temperature for 30 min. and iodomethane (6.81 g) was added to the reaction mixture. The mixture was further 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-methyl-5-(4-nitrobenzylidene)-1,3-thiazolidine-2,4-dione as yellow crystals (4.02 g, yield 95%). Recrystallization thereof from tetrahydrofuran-hexane gave yellow prism crystals. melting point: 233-234° C.

Workup

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

Sources & evidence

ORD record
ord-58d9896ce3534fa78d667cefdacaf09b
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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