Thionyl Chloride → 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride

Reaction equation

O[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][N:4]=1.S(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][N:4]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 229386294-Propyl-4H-1,2,4-triazole-3-methanol

Product 1

HCID 229387553-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride

Procedure

To 3-hydroxymethyl-4-propyl-4H-1,2,4-triazole (5.95 g), thionyl chloride (40 ml) was slowly added at 0° C. The mixture was heated to reflux for 1 hour, and concentrated under reduced pressure. To the residue was added ethanol, and the mixutre was further concentrated. To the residue were added ethyl acetate and small amount of ethanol, and the precipitated crystals were collected by filtration. The crystals were washed with ethyl acetate, to give 3-chloromethyl-4-propyl-4H-1,2,4-triazole hydrochloride (5.43 g) as pale yellow crystals.

Workup

temperatureThe mixture was heated
temperatureto reflux for 1 hour
concentrationconcentrated under reduced pressure
additionTo the residue was added ethanol
concentrationthe mixutre was further concentrated
additionTo the residue were added ethyl acetate and small amount of ethanol
filtrationthe precipitated crystals were collected by filtration
washThe crystals were washed with ethyl acetate

Sources & evidence

ORD record: ord-0b0d97d4c55d4af59975b87bece5e632
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262185B2

Reaction notes

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