2-Chloromethyl-4,5-dimethoxypyridinium chloride → HCID 178493770, compound

HRID 845512Notes

Reaction equation

HRID 845512 reaction equation
[Cl-].Cl[CH2:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][NH+:5]=1.[SH:14][C:15]1[NH:19][C:18]2[CH:20]=[CH:21][C:22]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:23][C:17]=2[N:16]=1>C(O)C.[OH-].[Na+]>[CH3:11][O:10][C:8]1[C:7]([O:12][CH3:13])=[CH:6][N:5]=[C:4]([CH2:3][S:14][C:15]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:23][C:17]=3[N:16]=2)[CH:9]=1

Participants

5

Reactant 2

HCID 201313622-Chloromethyl-4,5-dimethoxypyridinium chlorideHCID 178506357HCID 178506357, compound

Product 1

HCID 178493770HCID 178493770, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

1.57 g of 2-chloromethyl-4,5-dimethoxypyridinium chloride are added to a solution of 1.64 g of 2-mercapto-5-trifluoromethoxy-1H-benzimidazole in 40 ml of ethanol and 20 ml of 1N sodium hydroxide solution, the mixture is stirred at 20° C. for 2 hours and then at 40° C. for a further hour, the ethanol is distilled off on a rotary evaporator (10 mbar/40° C.) and the colorless precipitate which thereby separates out is filtered off over a suction filter, rinsed with 1N sodium hydroxide solution and water and dried. 2.15 g (79% of theory) of the title compound of m.p. 92°-93° C. are obtained.

Workup

  1. waitat 40° C. for a further hour
  2. distillationthe ethanol is distilled off on a rotary evaporator (10 mbar/40° C.)
  3. filtrationthe colorless precipitate which thereby separates out is filtered off over a suction
  4. filtrationfilter
  5. washrinsed with 1N sodium hydroxide solution and water
  6. customdried

Sources & evidence

ORD record
ord-7378c850cd6149cab38de33d634da51c
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

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