Ethyl Thioglycolate → 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole

HRID 485343ノート

反応式

HRID 485343 の反応式
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17]2)[CH:11]=1.[C:25]1(S(OCCC)(=O)=O)[CH:30]=CC=C[CH:26]=1>CN(C)C=O.O>[CH2:6]([O:5][C:3]([CH2:2][S:1][CH2:26][CH2:25][CH2:30][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([C:12]2[CH:11]=[N:10][CH:15]=[CH:14][CH:13]=2)[CH:17]=1)=[O:4])[CH3:7]

参加物

6

反応物 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 86740258N-(3-pyridyl)indole 3-propyl benzenesulfonate

生成物 1

HCID 202701983-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 0.36 g of ethyl mercaptoacetate in 20 ml of dimethylformamide is treated with 0.145 g of a 50% oil dispersion of sodium hydride at room temperature under nitrogen for 15 minutes. A solution of 1.13 g of N-(3-pyridyl)indole-3-propyl benzenesulfonate in 5 ml of dimethylformamide is added at room temperature. The reaction mixture is stirred for 15 hours, diluted with 100 ml of water and extracted 4 times with 50 ml of ethyl ether. The organic extracts are washed with 50 ml of water and 20 ml of cold 1N hydrochloric acid. The acid phase is extracted with ether and brought to pH=8.5 with 50% sodium hydroxide solution. The aqueous phase is extracted with chloroform (3×30 ml). The chloroform extract is dried over potassium carbonate and evaporated to yield 3-[3-(ethoxycarbonylmethylthio)propyl]-N-(3-pyridyl)indole; IR (CH2Cl2) 1725 cm-1.

後処理

  1. extractionextracted 4 times with 50 ml of ethyl ether
  2. washThe organic extracts are washed with 50 ml of water and 20 ml of cold 1N hydrochloric acid
  3. extractionThe acid phase is extracted with ether
  4. extractionThe aqueous phase is extracted with chloroform (3×30 ml)
  5. extractionThe chloroform extract
  6. dry with materialis dried over potassium carbonate
  7. customevaporated

出典と根拠

ORDレコード
ord-521735bd8390406ea7297250b6ab968e
出典データセット
uspto-grants-1985_08
特許番号
US04536505

反応ノート

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