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

HRID 30643ノート

反応式

HRID 30643 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-58d9896ce3534fa78d667cefdacaf09b
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

反応ノート

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