2-[[(4-Methoxy-3-methyl-2-pyridinyl)methyl]thio]-1H-benzimidazole → HCID 178431607, compound

HRID 1033739Notes

Reaction equation

HRID 1033739 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:12][C:13]3[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[C:4]=1[CH3:20]>Br>[OH:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][S:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[N:12]=2)[C:4]=1[CH3:20]

Participants

3

Reactant 1

HCID 108030672-[[(4-Methoxy-3-methyl-2-pyridinyl)methyl]thio]-1H-benzimidazole

Product 1

HCID 178431607HCID 178431607, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 2-[(4-methoxy-3-methyl-2-pyridyl) methylthio]benzimidazole (16.6 g) in 47% aqueous solution of HBr (250 ml) was heated for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure. The concentrate was neutralized with a saturated aqueous solution of sodium hydrogencarbonate. The oily portion was separated and subjected to a silica gel column chromatography, eluting with chloroform-methanol (25:2, v/v), to give 2-[(4-hydroxy-3-methyl-2-pyridyl)methylthio]benzimidazole (10.8 g) as colorless powder. 1H-NMR(δ ppm in CDCl3): 2.12(3H,s), 4.38(2H,s), 6.43(1H,d,J=7Hz), 7.1-7.3(2H,m), 7.4-7.6(3H,m)

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe oily portion was separated
  4. washeluting with chloroform-methanol (25:2

Sources & evidence

ORD record
ord-690521f704704beca8155296990c8d5e
Source dataset
uspto-grants-1994_05
Patent number
US05312824

Reaction notes

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