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

HRID 1654175Notes

Reaction equation

HRID 1654175 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:11]([CH3:12])[CH:10]=[N:9][N:8]=1>>[ClH:3].[Cl:3][CH2:6][C:7]1[N:11]([CH3:12])[CH:10]=[N:9][N:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 15707893(4-methyl-4H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 223819093-(chloromethyl)-4-methyl-4H-1,2,4-triazole hydrochloride

Procedure

To thionyl chloride (2.0 ml) was added at 0° C. 3-hydroxymethyl-4-methyl-4H-1,2,4-triazole (0.15 g), and the mixture was refluxed for 1.5 hour. The reaction mixture was concentrated under reduced pressure, to which was added diethyl ether. Resulting crystals were collected by filtration and dissolved in ethanol, to which was added diethyl ether for recrystallization to afford 3-chloromethyl-4-methyl-4H-1,2,4-triazole hydrochloride (0.22 g) as colorless prisms, m.p. 96°-97° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to which
  2. additionwas added diethyl ether
  3. customResulting crystals
  4. filtrationwere collected by filtration
  5. dissolutiondissolved in ethanol, to which
  6. additionwas added diethyl ether
  7. customfor recrystallization

Sources & evidence

ORD record
ord-a3b94bad97f84c95a707606a77dcd282
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

Loading…