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

HRID 845522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 845522
[OH-].[Na+].[F:3][C:4]1([F:17])[O:16][C:7]2=[CH:8][C:9]3[NH:13][C:12]([SH:14])=[N:11][C:10]=3[CH:15]=[C:6]2[O:5]1.[Cl-].Cl[CH2:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][NH+:22]=1>C(O)C.O>[F:17][C:4]1([F:3])[O:16][C:7]2=[CH:8][C:9]3[NH:13][C:12]([S:14][CH2:20][C:21]4[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][N:22]=4)=[N:11][C:10]=3[CH:15]=[C:6]2[O:5]1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 201313622-Chloromethyl-4,5-dimethoxypyridinium chlorideHCID 178506005HCID 178506005, Verbindung

Produkt 1

HCID 151635072,2-Difluoro-6-[(4,5-dimethoxy-2-pyridyl)methylthio]-5H-[1,3]-dioxolo[4,5-f]benzimidazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

6.3 ml of 1N sodium hydroxide solution are added dropwise to a solution, warmed to 50° C., of 0.69 g of 2,2-difluoro-5H-[1,3]-dioxolo[4,5-f]benzimidazole-6-thiol and 0.67 g of 2-chloromethyl-4,5-dimethoxypyridinium chloride in 9 ml of ethanol and 4 ml of water in the course of one minute. On cooling the clear reaction mixture to 20° C., a colorless precipitate separates out after a short time. The mixture is stirred at 20° C. for a further 5 hours and the precipitate is filtered off with suction over a suction filter, rinsed with 1N sodium hydroxide solution and water and dried to constant weight. The beige solid is dissolved in 10 ml of methylene chloride, insoluble constituents are filtered off, the filtrate is concentrated and the residue is made to crystallize by addition of diisopropyl ether after cooling. 1.02 g (90% of theory) of the title compound of m.p. 189°-191° C. are obtained.

Aufarbeitung

  1. filtrationthe precipitate is filtered off with suction over a suction
  2. filtrationfilter
  3. washrinsed with 1N sodium hydroxide solution and water
  4. customdried to constant weight
  5. dissolutionThe beige solid is dissolved in 10 ml of methylene chloride
  6. filtrationinsoluble constituents are filtered off
  7. concentrationthe filtrate is concentrated
  8. customto crystallize by addition of diisopropyl ether
  9. temperatureafter cooling

Quellen und Nachweise

ORD-Eintrag
ord-91ab30a450ac420ea1f1def09b6466cd
Quelldatensatz
uspto-grants-1988_07
Patentnummer
US04758579

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