Thionyl Chloride → 2-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride

HRID 1081683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1081683
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14]O)[C:9]=1[CH3:16].S(Cl)([Cl:19])=O>ClCCl>[ClH:19].[Cl:19][CH2:14][C:10]1[C:9]([CH3:16])=[C:8]([S:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][N:11]=1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 186900004-(2-Furylmethylthio)-2-hydroxymethyl-3-methylpyridine

Produkt 1

HCID 224607712-Chloromethyl-4-(2-furylmethylthio)-3-methylpyridine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

10.0 g (0.042 mol) of 4-(2-furylmethylthio)-2-hydroxymethyl-3-methylpyridine are dissolved in dichloromethane (100 ml), 1.2 equivalents of thionyl chloride are added dropwise at RT, and the mixture is stirred at RT for 20 h. The mixture is concentrated fully, which gives the title compound as an oily residue which crystallizes slowly and which, if desired, can also be used directly as a solution in ethanol for the reaction with substituted 2-mercaptobenzimidazoles. For purification, it is recrystallized from hot isopropanol with an addition of active charcoal. This gives 9.0 g (74% of theory) of the title compound as colorless crystals of m.p. 159°-161° C. (decomp.).

Aufarbeitung

  1. concentrationThe mixture is concentrated fully

Quellen und Nachweise

ORD-Eintrag
ord-5457d730b27b4526a6b8e156364895bb
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05587389

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