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

HRID 5435

Reaction equation

HRID 5435 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% potassium hydroxide (69.3 g, 105 mmoles) and dimethylsulfoxide (50 ml) was added S-[3-(amino)propyl]isothiourea.dihydrobromide (8.85 g, 39 mmoles) and the mixture was stirred at room temperature for 1.5 hours. To the reaction solution was added 5-chloroimidazo[1,2-a]pyridine (3.05 g, 20 mmoles), followed by stirring at room temperature for 1.5 hours and additional stirring at 65° C. for 20 hours. Water was added to the reaction solution, which was extracted with chloroform, washed several times with 1N-sodium chloride and dried over anhydrous magnesium sulfate. After 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 for 1.5 hours
  2. stirringadditional stirring at 65° C. for 20 hours
  3. extractionwas extracted with chloroform
  4. washwashed several times with 1N-sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationAfter the solvent was distilled off

Sources & evidence

ORD record
ord-cb1bba4ddd074106a9df010f3e7867aa
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Linked notes

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