Benzenepropanal → 5-(3-Phenylpropylidene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

HRID 357093

反応式

HRID 357093 の反応式
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]3[C:19](=[O:20])[CH2:18][O:17][C:16]3=[O:21])=[CH:8][CH:7]=[CH:6][C:5]=12.N1CCCC1.[C:27]1([CH2:33][CH2:34][CH:35]=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C>[C:27]1([CH2:33][CH2:34][CH:35]=[C:18]2[O:17][C:16](=[O:21])[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][S:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:19]2=[O:20])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 7707Benzenepropanal2 回HCID 31268Pyrrolidine2 回HCID 189367363-[4-(Imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

生成物 1

HCID 572607645-(3-Phenylpropylidene)-3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

反応条件

温度
60 °C

実験手順

1.53 g (5 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione and 20 ml of ethanol were placed in a reaction flask, followed by stirring at 60° C. for 20 minutes, to dissolve the starting materials. After this mixture was kept standing to 50° C., an ethanol solution of 0.05 ml (0.5 mmol) of pyrrolidine was added. Next, an ethanol solution of 0.66 ml (5 mmol) of 3-phenylpropionaldehyde was added, followed by refluxing for 19 hours. Six hours later, 0.66 ml (5 mmol) of 3-phenylpropionaldehyde and 0.05 ml (0.5 mmol) of pyrrolidine were added. After the reaction mixture was cooled, the solvent was distilled off, followed by extraction with dichloromethane and water. After the organic layer was dried with sodium sulfate, the solvent was distilled off. The residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/1) to yield 26 mg (1.2%, yellow oily substance) of the desired product.

後処理

  1. dissolutionto dissolve the starting materials
  2. customwas kept standing to 50° C.
  3. temperatureby refluxing for 19 hours
  4. temperatureAfter the reaction mixture was cooled
  5. distillationthe solvent was distilled off
  6. extractionfollowed by extraction with dichloromethane and water
  7. dry with materialAfter the organic layer was dried with sodium sulfate
  8. distillationthe solvent was distilled off
  9. washThe residue was eluted by column chromatography (eluent, hexane/ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-dcae2e9c56c2411b9f4c9ab2d1acd2d0
出典データセット
uspto-grants-1998_11
特許番号
US05840732

関連ノート

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