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

HRID 1871946Notes

Reaction equation

HRID 1871946 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>C(Cl)Cl>[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 methylene chloride (100 ml), 1.2 equivalents of thionyl chloride are added dropwise at RT and the mixture is stirred at RT for 20 h. It is concentrated completely and the title compound is obtained as an oily residue, which gradually crystallizes and, if desired, can also be used as a solution in ethanol directly for reaction with substituted 2-mercaptobenzimidazoles. For purification, the residue is recrystallized from hot isopropanol with the addition of active charcoal. 9.0 g (74% of theory) of the title compound are obtained as colorless crystals of m.p. 159-161° C. (decomp.).

Workup

  1. concentrationIt is concentrated completely

Sources & evidence

ORD record
ord-de78e19098984122a5e4b29c6decc1ab
Source dataset
uspto-grants-2000_08
Patent number
US06107312

Reaction notes

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