Thionyl Chloride → 4-(2-(N-benzyl-N-methylamino)ethylthio)-2-chloromethyl-3-methylpyridine

HRID 52140Notes

Reaction equation

HRID 52140 reaction equation
[CH2:1]([N:8]([CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19]O)[C:14]=1[CH3:21])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>>[CH2:1]([N:8]([CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH2:19][Cl:24])[C:14]=1[CH3:21])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 199629754-(2-(N-benzyl-N-methylamino)ethylthio)-2-hydroxymethyl-3-methylpyridine

Product 1

HCID 199630684-(2-(N-benzyl-N-methylamino)ethylthio)-2-chloromethyl-3-methylpyridine

Procedure

Thionyl chloride (10 ml) was dropwise added to 4-(2-(N-benzyl-N-methylamino)ethylthio)-2-hydroxymethyl-3-methylpyridine (1.8 g) under ice-cooling and the mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, 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 1.7 g of 4-(2-(N-benzyl-N-methylamino)ethylthio)-2-chloromethyl-3-methylpyridine. The product was added to ethanol (30 ml) containing a solution of 2-mercaptobenzimidazole (0.9 g) and sodium hydroxide (0.5 g) in water (10 ml) and the mixture was refluxed under heating for 7 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 acetone-isopropyl ether to give 2-((4-(2-(N-benzyl-N-methylamino)ethylthio)-3-methyl-2-pyridyl)methylthio)-1H-benzimidazole as crystals, melting point 110°-112° C.

Workup

  1. temperaturecooling
  2. distillationwas distilled away
  3. extractionextracted with chloroform
  4. dry with materialThe chloroform layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

Sources & evidence

ORD record
ord-0c601871e17446918b12864b5b0233f4
Source dataset
uspto-grants-1997_04
Patent number
US05616581

Reaction notes

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