Dimethylamine → 5-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

HRID 357151ノート

反応式

HRID 357151 の反応式
[CH2:1]=O.[CH3:3][NH:4][CH3:5].[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9].[OH-].[Na+]>C(O)(=O)C>[CH:6](=[C:10]1[S:14][C:13](=[O:15])[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][S:20][C:21]2[N:26]3[C:27]([CH2:3][N:4]([CH3:1])[CH3:5])=[CH:28][N:29]=[C:25]3[CH:24]=[CH:23][CH:22]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9]

参加物

6

反応物 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 569791215-Butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

生成物 1

HCID 570724355-Butylidene-3-[4-(3-dimethylaminomethylimidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

反応条件

温度
80 °C

実験手順

To a solution of 0.27 ml (3.6 mmol) of formalin and 0.33 g (3.6 mmol) of a 50% aqueous dimethylamine solution in 20 ml of acetic acid, a solution of 1.13 g (3.0 mmol) of 5-butylidene-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]thiazolidine-2,4-dione in 5 ml of acetic acid was added at 0° C., followed by stirring at 80° C. for 90 minutes. After cooling, the reaction mixture was poured into 50 ml of 50% aqueous sodium hydroxide under ice cooling conditions. The mixture was extracted with chloroform and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform/methanol=25/1) to yield 0.43 g (33.3%, yellow oily substance) of the desired product.

後処理

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with chloroform
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, chloroform/methanol=25/1)

出典と根拠

ORDレコード
ord-fad4aecc3c424606b99c8356a387d768
出典データセット
uspto-grants-1998_11
特許番号
US05840732

反応ノート

読み込み中…