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

HRID 1081754

반응식

HRID 1081754 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-01a9dccd1660474494a1ab63880b1b56
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05587383

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