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

HRID 5482

Reaction equation

HRID 5482 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c26cb13241bf43e2bb978f5ffb81ffc1
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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