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

HRID 1081683Notes

Reaction equation

HRID 1081683 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  1. concentrationThe mixture is concentrated fully

Sources & evidence

ORD record
ord-5457d730b27b4526a6b8e156364895bb
Source dataset
uspto-grants-1996_12
Patent number
US05587389

Reaction notes

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