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

HRID 327780Notes

Reaction equation

HRID 327780 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>CO.O>[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. customwas dried over MGSO4
  7. customevaporated
  8. customgiving an oil which
  9. customwas purified on silica gel (50 g)

Sources & evidence

ORD record
ord-1b47bfea670c41e2a9109aecc1fd0cf1
Source dataset
uspto-grants-1993_12
Patent number
US05274099

Reaction notes

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