2-(Chloromethyl)-4-methoxypyridine hydrochloride → 4-Fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1756610Notes

Reaction equation

HRID 1756610 reaction equation
[F:1][C:2]1[C:10]2[N:9]=[C:8]([SH:11])[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH2:21]Cl)[CH:16]=1>O.CO>[F:1][C:2]1[C:10]2[N:9]=[C:8]([S:11][CH2:21][C:17]3[CH:16]=[C:15]([O:14][CH3:13])[CH:20]=[CH:19][N:18]=3)[NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochlorideHCID 178505573HCID 178505573, compound

Product 1

HCID 156624884-Fluoro-2-[[(4-methoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of 4-fluoro-2-mercapto-1H-benzimidazole (1.15 g, 0.0068 mol) in methanol (60 ml) NaOH (0.54 g, 0.014 mol) dissolved in water (3 ml) and 4-methoxy-2-chloromethylpyridine hydrochloride (1.32 g, 0.0068 mol) dissolved in methanol (20 ml) were added in the given order. The mixture was refluxed for one hour whereupon the solution was evaporated. The residue was partitioned between methylene chloride and water. After separation the organic solution was dried over MgSO4 and evaporated giving an oil which was purified on silica gel (50 g) using 1% methanol in methylene chloride as eluent. In this way the title compound was obtained (1.35 g, 69%). NMR data for the product is given below.

Workup

  1. additionwere added in the given order
  2. temperatureThe mixture was refluxed for one hour whereupon the solution
  3. customwas evaporated
  4. customThe residue was partitioned between methylene chloride and water
  5. customAfter separation the organic solution
  6. dry with materialwas dried over MgSO4
  7. customevaporated
  8. customgiving an oil which
  9. customwas purified on silica gel (50 g)

Sources & evidence

ORD record
ord-2ce8850fd0c5429984b9f6fac259b628
Source dataset
uspto-grants-1995_08
Patent number
US05441968

Reaction notes

Loading…