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

HRID 856647Notes

Reaction equation

HRID 856647 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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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

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

Sources & evidence

ORD record
ord-0b0d97d4c55d4af59975b87bece5e632
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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