HCID 19024498, compound → HCID 178431608, compound

HRID 1033740Notes

Reaction equation

HRID 1033740 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([O:18]C)[CH:14]=[CH:13][N:12]=3)[NH:8][C:4]=2[CH:3]=1>Br>[F:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([S:9][CH2:10][C:11]3[C:16]([CH3:17])=[C:15]([OH:18])[CH:14]=[CH:13][N:12]=3)[NH:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 19024498HCID 19024498, compound

Product 1

HCID 178431608HCID 178431608, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 5-fluoro-2-[(4-methoxy-3-methyl-2-pyridyl)methylthio]benzimidazole (5.5 g) in aqueous 47% HBr (50 ml) was heated for 24 hours under reflux. The reaction mixture was concentrated under reduced pressure. The residual oily substance was neutralized with a saturated aqueous solution of sodium hydrogencarbonate, to which was added ethyl acetate (50 ml) to give 5-fluoro-2-[(4-hydroxy-3-methyl-2-pyridyl)methylthio]benzimidazole (3.2 g, 62%). Recrystallization from ethanol afforded colorless needles, mp 232°-233° C.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionwas added ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-ffd857dc0bfe46479595f5a5ce73f935
Source dataset
uspto-grants-1994_05
Patent number
US05312824

Reaction notes

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