Water → HCID 178493767, compound

HRID 845515Notes

Reaction equation

HRID 845515 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:10][C:4]=2[N:3]=1.[Cl-].Cl[CH2:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[CH:22][NH+:21]=1.O>C(O)C.[OH-].[Na+]>[CH3:27][O:26][C:24]1[C:23]([O:28][CH3:29])=[CH:22][N:21]=[C:20]([CH2:19][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]([F:16])([F:14])[F:15])=[CH:10][C:4]=3[N:3]=2)[CH:25]=1

Participants

6

Reactant 3

HCID 962WaterHCID 201313622-Chloromethyl-4,5-dimethoxypyridinium chlorideHCID 178506345HCID 178506345, compound

Product 1

HCID 178493767HCID 178493767, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

1.0 g of 2-mercapto-5-(2,2,2-trifluoroethoxy)-1H-benzimidazole is dissolved in 15 ml of ethanol and 8.5 ml of 1N sodium hydroxide solution, 0.90 g of 2-chloromethyl-4,5-dimethoxypyridinium chloride are added and the mixture is stirred for 20 hours. After addition of 30 ml of water, the mixture is extracted three times with 30 ml of methylene chloride each time, the methylene chloride phase is washed once with 5 ml of 0.1N sodium hydroxide solution, the combined organic phases are dried over magnesium sulfate and, after the drying agent has been filtered off, the filtrate is completely concentrated. 1.51 g (94% of theory) of the title compound are obtained as an amorphous solid residue of m.p. 55°-57° C.

Workup

  1. extractionthe mixture is extracted three times with 30 ml of methylene chloride each time
  2. washthe methylene chloride phase is washed once with 5 ml of 0.1N sodium hydroxide solution
  3. dry with materialthe combined organic phases are dried over magnesium sulfate
  4. filtrationafter the drying agent has been filtered off
  5. concentrationthe filtrate is completely concentrated

Sources & evidence

ORD record
ord-6b38d607ed584f6d874e70a98ec97057
Source dataset
uspto-grants-1988_07
Patent number
US04758579

Reaction notes

Loading…