Dimethyl Sulfoxide → 5-[3-(Amino)propylthio]imidazo[1,2-a]pyridine

HRID 5482ノート

反応式

HRID 5482 の反応式
[OH-].[K+].CS(C)=O.Br.Br.[NH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14](=[NH:16])N.ClC1[N:23]2[CH:24]=[CH:25]N=[C:22]2[CH:21]=[CH:20][CH:19]=1>O>[NH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14]1[N:16]2[CH:25]=[CH:24][N:23]=[C:22]2[CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 14797Potassium HydroxideHCID 145992Pseudourea, 2-(3-aminopropyl)-2-thio-, dihydrobromideHCID 109537225-Chloroimidazo[1,2-A]pyridine

生成物 1

HCID 233628495-[3-(Amino)propylthio]imidazo[1,2-a]pyridine収率 64.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixed solution of 10% (w/w) potassium hydroxide (69.3 g, 105 mmoles) and dimethylsulfoxide (50 ml) was added S-(3-aminopropyl)isothiourea dihydrobromide (8.85 g, 39 mmoles) and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added 5-chloroimidazo[1,2-a]pyridine (3.05 g, 20 mmoles), followed by stirring at room temperature and additionally at 65° C. for 20 hours. Water was added to the reaction mixture, which was extracted with chloroform, washed with 1N sodium hydroxide several times and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off to obtain 2.66 g of the desired product (64.3%, pale yellow oily product).

後処理

  1. stirringby stirring at room temperature and additionally at 65° C. for 20 hours
  2. extractionwas extracted with chloroform
  3. washwashed with 1N sodium hydroxide several times
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off

出典と根拠

ORDレコード
ord-c26cb13241bf43e2bb978f5ffb81ffc1
出典データセット
uspto-grants-1993_09
特許番号
US05244908

反応ノート

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