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

HRID 1983031Notes

Reaction equation

HRID 1983031 reaction equation
[C:1]([C:5]1[N:9]=[CH:8][N:7]([CH2:10]O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:14])=O>>[ClH:14].[C:1]([C:5]1[N:9]=[CH:8][N:7]([CH2:10][Cl:14])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 577124183-t-butyl-1H-1,2,4-triazole1-ylmethanol

Product 1

HCID 231491201-(chloromethyl)-3-t-butyl-1H-1,2,4-triazole hydrochloride

Procedure

The mixture of 1.38 g of 3-t-butyl-1H-1,2,4-triazole1-ylmethanol and 2.7 ml of thionyl chloride was stirred under reflux condition for 3 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was recrystallized from hexane to obtain 1.72 g of 3-t-butyl-1-(chloromethyl)-1H-1,2,4-triazole hydrochloride. 1H-NMR (CDCl3, TMS, δ (ppm)): 1.36 (9H, s), 5.83 (2H, s), 8.17 (1H, s)

Workup

  1. temperatureunder reflux condition for 3 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-0233433b0e7c40e2b7795291e72393a0
Source dataset
uspto-grants-2009_06
Patent number
US07541374B2

Reaction notes

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