Water → 2,2-Difluoro-6-[(4,5-dimethoxy-3-methyl-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

HRID 845519Notes

Reaction equation

[Cl-].Cl[CH2:3][C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([O:13][CH3:14])=[CH:6][NH+:5]=1.[F:15][C:16]1([F:29])[O:28][C:19]2=[CH:20][C:21]3[NH:25][C:24]([SH:26])=[N:23][C:22]=3[CH:27]=[C:18]2[O:17]1.O>C(O)C.[OH-].[Na+]>[F:29][C:16]1([F:15])[O:28][C:19]2=[CH:20][C:21]3[NH:25][C:24]([S:26][CH2:3][C:4]4[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([O:13][CH3:14])=[CH:6][N:5]=4)=[N:23][C:22]=3[CH:27]=[C:18]2[O:17]1

Participants

Conditions

Temperature: 20 °C

Procedure

0.96 g of 2-chloromethyl-4,5-dimethoxy-3-methylpyridinium chloride are added to a solution of 0.92 g of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol in 10 ml of ethanol and 10 ml of 1N sodium hydroxide solution. The yellow reaction mixture is stirred at 20° C. for 1 hour, a further 10 ml of water are added, whereupon a colorless solid precipitates out, the mixture is stirred for a further 5 hours and filtered and the residue is rinsed with 1N sodium hydroxide solution and water and dried to constant weight. The amorphous powder is recrystallized from methylene chloride/diisopropyl ether. 1.5 g (93% of theory) of the title compound are obtained in the form of colorless crystals of m.p. 160°-161° C.

Workup

customprecipitates out, the mixture
stirringis stirred for a further 5 hours
filtrationfiltered
washthe residue is rinsed with 1N sodium hydroxide solution and water
customdried to constant weight
customThe amorphous powder is recrystallized from methylene chloride/diisopropyl ether

Sources & evidence

ORD record: ord-0a167d16478848fc825edaca4e45c9d4
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04758579

Reaction notes

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