Butanal → 5-Butylidene-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

HRID 357193ノート

反応式

HRID 357193 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][S:17][C:16]3=[O:21])[C:5]=12.[CH:22](=O)[CH2:23][CH2:24][CH3:25].N1CCCC1>C(O)C>[CH:22](=[C:18]1[S:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:6]2[C:5]3[N:4]([CH:3]=[CH:2][N:1]=3)[CH:9]=[CH:8][CH:7]=2)[C:19]1=[O:20])[CH2:23][CH2:24][CH3:25]

参加物

5

反応物 3

HCID 261Butanal2 回HCID 31268Pyrrolidine2 回HCID 189368403-[4-(Imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

生成物 1

HCID 572057075-Butylidene-3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1.25 g (4.32 mmol) of 3-[4-(imidazo[1,2-a]pyridin-8-yloxy)butyl]thiazolidine-2,4-dione and 0.39 ml (4.32 mmol) of 1-butanal in 20 ml of ethanol, 0.036 ml (0.43 mmol) of pyrrolidine was added at 60° C., followed by refluxing for 19 hours (1 and 2 hours later, 0.39 ml (4.32 mmol) was further added; 3 hours later, 0.39 ml (4.32 mmol) of 1-butanal and 0.036 ml (0.43 mmol) of pyrrolidine were further added). After the reaction mixture was cooled, the solvent was distilled off. The residue was dissolved in dichloromethane, washed with purified water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4), after which the solvent was distilled off, to yield 0.17 g (11.5%, yellow oily substance) of the desired product.

後処理

  1. temperatureby refluxing for 19 hours (1 and 2 hours later
  2. addition0.39 ml (4.32 mmol) was further added
  3. temperatureAfter the reaction mixture was cooled
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with purified water
  7. customdried
  8. distillationafter which the solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent, n-hexane/ethyl acetate=1/4)
  10. distillationafter which the solvent was distilled off

出典と根拠

ORDレコード
ord-f5f6c629edd142e69c040bd38c16b828
出典データセット
uspto-grants-1998_11
特許番号
US05840732

反応ノート

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