Thionyl Chloride → 5-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

HRID 1654173Notes

Reaction equation

HRID 1654173 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:11]([CH3:12])[N:10]=[CH:9][N:8]=1>>[ClH:3].[Cl:3][CH2:6][C:7]1[N:11]([CH3:12])[N:10]=[CH:9][N:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11073377(1-methyl-1H-1,2,4-triazol-5-yl)methanol

Product 1

HCID 222853325-(chloromethyl)-1-methyl-1H-1,2,4-triazole hydrochloride

Procedure

To thionyl chloride (8.0 ml) was gradually added 5-hydroxymethyl-1-methyl-1H-1,2,4-triazole (0.80 g) at 0° C., followed by refluxing for 3 hours. The reaction mixture was concentrated under reduced pressure. To the concentrate was added diethyl ether, then resulting powdery product was collected by filtration. The powdery product was dissolved in ethanol, to which was added diethyl ether to cause crystallization to afford 5-chloromethyl-1-methyl-1H-1,2,4-triazole hydrochloride (1.1 g) as colorless plates, m.p. 77°-78° C.

Workup

  1. customat 0° C.
  2. temperatureby refluxing for 3 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the concentrate was added diethyl ether
  5. filtrationresulting powdery product was collected by filtration
  6. dissolutionThe powdery product was dissolved in ethanol, to which
  7. additionwas added diethyl ether
  8. customcrystallization

Sources & evidence

ORD record
ord-454976644c904f4d942110050ae30091
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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