Sodium Hydroxide → 1,8-Dihydro-2-[[(5-methyl-2-pyridyl)methyl]thio]-m-dioxino(4,5-f)benzimidazole dihydrochloride

HRID 745591

Reaktionsgleichung

Reaktionsgleichung von HRID 745591
[NH:1]1[C:5]2[CH:6]=[C:7]3[CH2:13][O:12][CH2:11][O:10][C:8]3=[CH:9][C:4]=2[N:3]=[C:2]1[SH:14].[OH-].[Na+].[ClH:17].[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][Cl:26])=[N:23][CH:24]=1>O>[ClH:26].[ClH:17].[CH3:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][S:14][C:2]2[NH:1][C:5]3[CH:6]=[C:7]4[CH2:13][O:12][CH2:11][O:10][C:8]4=[CH:9][C:4]=3[N:3]=2)=[N:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 233137952-(Chloromethyl)-5-methylpyridine hydrochlorideHCID 178527751HCID 178527751, Verbindung

Produkt 1

HCID 704548491,8-Dihydro-2-[[(5-methyl-2-pyridyl)methyl]thio]-m-dioxino(4,5-f)benzimidazole dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To 3.7 g of 1,8-dihydro-m-dioxino(4,5-f)benzimidazole-2-thiol, suspended in 60 ml of alcohol, were added dropwise while stirring 1.5 g of sodium hydroxide in 30 ml of water and, after 30 minutes, there were added 3.4 g of 5-methyl-2-chloromethylpyridine hydrochloride. The mixture was left to boil at reflux overnight, then evaporated and the residue was taken up in methylene chloride. This mixture was washed first with 3N sodium hydroxide, then neutral with water, dried over sodium sulfate and evaporated in vacuo. The crude porduct was dissolved while heating in a small amount of methanol and treated with 25 ml of 5N hydrochloric acid in ethylacetate. There was obtained 1,8-dihydro-2-[[(5-methyl-2-pyridyl)methyl]thio]-m-dioxino(4,5-f)benzimidazole dihydrochloride of melting point 153°-155° C.

Aufarbeitung

  1. additionwere added dropwise
  2. waitThe mixture was left
  3. temperatureat reflux overnight
  4. customevaporated
  5. washThis mixture was washed first with 3N sodium hydroxide
  6. dry with materialneutral with water, dried over sodium sulfate
  7. customevaporated in vacuo
  8. dissolutionThe crude porduct was dissolved
  9. temperaturewhile heating in a small amount of methanol
  10. additiontreated with 25 ml of 5N hydrochloric acid in ethylacetate

Quellen und Nachweise

ORD-Eintrag
ord-e00a739f4fa644628b608610ef8b8b3f
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04599347

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