Thionyl Chloride → 2-Chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

HRID 1720045Notes

Reaction equation

HRID 1720045 reaction equation
O[CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:21])=O>>[Cl:21][CH2:2][C:3]1[C:8]([CH3:9])=[C:7]([S:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 199630392-Hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

Product 1

HCID 199630342-Chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine

Procedure

Thionyl chloride (20 ml) was dropwise added to 2-hydroxymethyl-3-methyl-4-(2-morpholinoethylthio)pyridine (2 g) under ice-cooling and the mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, the thionyl chloride was distilled away. The residue was alkali-oversaturated with potassium carbonate and extracted with chloroform. The chloroform layer was dried over anhydrous magnesium sulfate and the solvent was distilled away to give 2.1 g of 2-chloromethyl-3-methyl-4-(2-morpholinoethylthio)pyridine as an oily substance. The oily substance was added to ethanol (50 ml) containing a solution of 2-mercaptobenzimidazole (1.0 g) and sodium hydroxide (0.6 g) in water (10 ml) and the mixture was refluxed under heating for 5 hours. After the completion of the reaction, the ethanol was distilled away and water was added to the residue, followed by extraction with chloroform. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled away. Acetone was added to the residue to allow crystallization. The obtained crystals were recrystallized from a mixed solvent of ethanol-acetone to give 2-((3-methyl-4-(2-morpholinoethylthio)-2-pyridyl)methylthio)-1H-benzimidazole as white crystals, melting point 201°-203° C.

Workup

  1. temperaturecooling
  2. customAfter the completion of the reaction
  3. distillationthe thionyl chloride was distilled away
  4. extractionextracted with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-3a0a6584bc934a6485ab3c081eb730c7
Source dataset
uspto-grants-1996_04
Patent number
US05504082

Reaction notes

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