2-(Chloromethyl)-3,4-dimethoxypyridin-1-ium chloride → HCID 178493203, compound

HRID 845518Notes

Reaction equation

[Cl-].Cl[CH2:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[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:30])([F:29])[CH:26]([F:28])[F:27])=[CH:23][C:17]=2[N:16]=1>C(O)C.O.[OH-].[Na+]>[CH3:11][O:10][C:9]1[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:30])([F:29])[CH:26]([F:28])[F:27])=[CH:23][C:17]=3[N:16]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 20 °C

Procedure

0.38 g (1.7 mmol) of 2-chloromethyl-3,4-dimethoxypyridinium chloride is added to a solution of 0.46 g (1.7 mmol) of 2-mercapto-5-(1,1,2,2-tetra fluoroethoxy)-1H-benzimidazole in 10 ml of ethanol, 10 ml of water and 1.8 ml of 2N sodium hydroxide solution; after the mixture has been stirred at 20° C. for one hour, a further 10 ml of water are added dropwise. The mixture is then stirred at 20° C. for a further four hours. The solid which has precipitated out is filtered off, washed with 0.01N sodium hydroxide solution and then with water until neutral and dried to constant weight. 0.63 g (90% of theory) of the title compound is obtained as a colorless crystalline powder of m.p. 98°-102° C.

Workup

stirringThe mixture is then stirred at 20° C. for a further four hours
customThe solid which has precipitated out
filtrationis filtered off
washwashed with 0.01N sodium hydroxide solution
dry with materialwith water until neutral and dried to constant weight

Sources & evidence

ORD record: ord-b61163aa447a43309b6dc8594a674096
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04758579

Reaction notes

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