Réaction #3342

Équation de réaction

2-chloromethylpyridine hydrochloride

5,5-dimethyl-2,4-dithiohydantoin

NaOH

→

2-(2-pyridylmethylthio)-5,5-dimethylimidazolin-4-thione

Conditions de réaction

Traitement

1. 1
   Extractionextracted with 100 mL of chloroform (CHCl3)
2. 2
   SéchageThe CHCl3 layer was dried over MgSO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   AutreThe residue was purified by column chromatography (
5. 5
   AutreAs a result, 2-(2-pyridylmethylthio) was initially obtained

Mode opératoire

Initially, 2.7 g of 2-chloromethylpyridine hydrochloride was added to a solution of 2.4g of 5,5-dimethyl-2,4-dithiohydantoin in 17 mL of 2N aqueous solution of NaOH. The reaction mixture was stirred for one hour at the room temperature, and extracted with 100 mL of chloroform (CHCl3). The CHCl3 layer was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (using CHCl3 as a developing solvent). As a result, 2-(2-pyridylmethylthio) was initially obtained. From the earlier fractions, the desired compound of 2-(2-pyridylmethylthio)-5,5-dimethylimidazolin-4-thione was isolated in the form of a syrup. The yield of this compound was 1.02 g with a yield ratio of 27.1%.

Source