Thionyl Chloride → 3-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Reaction equation

S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:11]=[CH:10][N:9]([CH3:12])[N:8]=1>>[ClH:3].[Cl:3][CH2:6][C:7]1[N:11]=[CH:10][N:9]([CH3:12])[N:8]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 10351670(1-Methyl-1H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 225069273-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Procedure

To thionyl chloride (8.0 ml) was gradually added at 0° C. 3-hydroxymethyl-1-methyl-1H-1,2,4-triazole (0.60 g), which was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure, to which was added diethyl ether. Resulting powder was crystallized from a mixture of ethanol and diethyl ether to give 3-chloromethyl-1-methyl-1H-1,2,4-triazole hydrochloride (1.0 g) as colorless needles, m.p. 69°-70° C.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure, to which
additionwas added diethyl ether
customResulting powder
customwas crystallized from a mixture of ethanol and diethyl ether

Sources & evidence

ORD record: ord-a8b190683172462ba1c7f73c873436d2
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05405861

Reaction notes

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