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

HRID 1647159
Notes
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Reaction equation

HRID 1647159 reaction equation
[C:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([SH:11])=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].Cl.[CH3:18][O:19][C:20]1[C:21]([CH2:28]Cl)=[N:22][CH:23]=[CH:24][C:25]=1[O:26][CH3:27]>O.C(O)C>[C:1]([C:4]1[C:13]([CH3:14])=[CH:12][C:7]2[NH:8][C:9]([S:11][CH2:28][C:21]3[C:20]([O:19][CH3:18])=[C:25]([O:26][CH3:27])[CH:24]=[CH:23][N:22]=3)=[N:10][C:6]=2[CH:5]=1)(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 162169282-Chloromethyl-3,4-dimethoxypyridinium chlorideHCID 178465846HCID 178465846, compound

Product 1

HCID 199264555-Acetyl-6-methyl-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]thio]-1H-benzimidazoleYield 62%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 962WaterSolvent2×

Procedure

5-Acetyl-6-methyl-2-mercapto-1H-benzimidazole (4.2 g, 20 mmol) and NaOH (0.8 g, 20 mmol) in H2O (1 ml) were dissolved in 60 ml ethanol. 3,4-dimethoxy-2-chloromethylpyridine hydrochloride (≈17 mmol) as a crude material was added and the mixture was heated to boiling. NaOH (0.7 g, 17 mmol) in H2O (1 ml) was added and the reflux was continued for 6 hours. The solvent was evaporated off and the residue was diluted with methylene chloride and water. The organic phase was dried over Na2SO4 and the solvent was removed under reduced pressure. Crystallizing from acetonitrile gave the title compound, (3.75 g, 62%).

Workup

  1. temperaturethe mixture was heated to boiling
  2. customThe solvent was evaporated off
  3. additionthe residue was diluted with methylene chloride and water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customthe solvent was removed under reduced pressure
  6. customCrystallizing from acetonitrile

Sources & evidence

ORD record
ord-ed7420d3632441a5b6436f3073b6bcbf
Source dataset
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05430042

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes