HCID 22321559, compound → 4-(chloromethyl)-1-methyl-1H-1,2,3-triazole hydrochloride

HRID 985444Notes

Reaction equation

HRID 985444 reaction equation
O.[ClH:2].[CH3:3][N:4]1[CH:8]=[C:7]([CH2:9]O)[N:6]=[N:5]1>S(Cl)(Cl)=O>[ClH:2].[Cl:2][CH2:9][C:7]1[N:6]=[N:5][N:4]([CH3:3])[CH:8]=1

Participants

3

Reactant 1

HCID 22321559HCID 22321559, compound

Product 1

HCID 223215554-(chloromethyl)-1-methyl-1H-1,2,3-triazole hydrochloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To thionyl chloride (20 ml) under nitrogen, cooled by an ice bath, was added (1-methyl-1H-[1,2,3]triazol-4-yl)methanol hydrochloride monohydrate (1.996 g, 11.9 mmol). The mixture was stirred for 5 min before removing the cooling bath and heating at reflux for 30 min. The excess thionyl chloride was evaporated in vacuo and the residue was triturated with diethyl ether. The resulting solid was collected by filtration, washed with diethyl ether and dried under vacuum at 60° C. to give the title compound as a white solid: 1H NMR (360 MHz, DMSO-d6) δ 4.04 (3H, s), 4.81 (2H, s), 8.13 (1H, s).

Workup

  1. custombefore removing the cooling bath
  2. temperatureheating
  3. temperatureat reflux for 30 min
  4. customThe excess thionyl chloride was evaporated in vacuo
  5. customthe residue was triturated with diethyl ether
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with diethyl ether
  8. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-2774937715ea49fd92305f4b40213359
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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