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

HRID 496553Notes

Reaction equation

HRID 496553 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 hydrochlorideYield 101.8%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

1-Methyl-4-hydroxymethyl-1,2,3-triazole hydrochloride hydrate (1.0 g, 6.08 mmol) was suspended in 20 ml thionyl chloride and the mixture was refluxed for 1 hour. Excess thionyl chloride was evaporated off and the residue was triturated with diethyl ether (25 ml). The white solid produced was washed by decantation with diethyl ether and dried in vacuo to give the required product (0.52 g, 51%). 1H NMR (360 MHz, d6-DMSO) 4.04 (3H, s), 4.82 (2H, s), 8.16 (1H, s); MS+131&133.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customExcess thionyl chloride was evaporated off
  3. customthe residue was triturated with diethyl ether (25 ml)
  4. customThe white solid produced
  5. washwas washed by decantation with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5e76d283ec8042c99a665206f2ec6185
Source dataset
uspto-grants-2005_09
Patent number
US06946461B2

Reaction notes

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