Sodium Hydroxide → 5-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazole

HRID 1647158Notes

Reaction equation

HRID 1647158 reaction equation
[C:1]([C:5]1[C:14]([CH3:15])=[CH:13][C:8]2[NH:9][C:10]([SH:12])=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2].[OH-].[Na+].Cl.[CH3:19][O:20][C:21]1[C:22]([CH2:29]Cl)=[N:23][CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>O.CO>[C:1]([C:5]1[C:14]([CH3:15])=[CH:13][C:8]2[NH:9][C:10]([S:12][CH2:29][C:22]3[C:21]([O:20][CH3:19])=[C:26]([O:27][CH3:28])[CH:25]=[CH:24][N:23]=3)=[N:11][C:7]=2[CH:6]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideHCID 178497010HCID 178497010, compound

Product 1

HCID 218515495-Carbomethoxy-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazoleYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

5-Carbomethoxy-6-methyl-2-mercapto-1H-benzimidazole (0.67 g, 0.003 mol) and NaOH (0.12g, 0.003 mol) in H2O (0.6 ml) were dissolved in CH3OH (15 ml). 3,4-dimethoxy-2-chloromethylpyridine hydrochloride, (=0.0036 mol) as a crude material in CH3OH (10 ml) and NaOH (0.144 g, 0.0036 mol) in H2O (0.72 ml) were added. The mixture was heated to reflux and the reflux was continued for 1 hour. CH3OH was evaporated off and the crude material was purified by chromatography on a silica column using CH2Cl2 --CH3OH (98-2) as eluent, giving (1.03 g, 92%) of the pure title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customCH3OH was evaporated off
  4. customthe crude material was purified by chromatography on a silica column

Sources & evidence

ORD record
ord-1ba172f79c6749f4bec328c1fa0be190
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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