Thionyl Chloride → 1-(4-Fluorophenyl)-4-methyl-5-chloromethyl-1,2,3-triazole

HRID 1090116Notes

Reaction equation

HRID 1090116 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13]O)=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][Cl:18])=[C:11]([CH3:15])[N:10]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 19914681(1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 199146751-(4-Fluorophenyl)-4-methyl-5-chloromethyl-1,2,3-triazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-(4-fluorophenyl)-4-methyl-5-hydroxymethyl-1,2,3-triazole (871 mg; 4.20 mmol), prepared as described in example 6, and thionyl chloride (400 ml; 5.46 mmol) in benzene (14 ml) was heated under reflux for 4 hours. The reaction mixture was kept under stirring at room temperature overnight, thionyl chloride and benzene were evaporated and the resultant crude compound was collected several times with benzene. After evaporation of the solvent, the crude compound was purified by chromatography on silica gel (230-400 mesh), eluent methylene chloride:acetone=95:5, giving the title compound (m.p. 70°-71° C.).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. customthionyl chloride and benzene were evaporated
  4. customthe resultant crude compound was collected several times with benzene
  5. customAfter evaporation of the solvent
  6. customthe crude compound was purified by chromatography on silica gel (230-400 mesh), eluent methylene chloride

Sources & evidence

ORD record
ord-dce0ef16f7bd487a8ff610c1e8344581
Source dataset
uspto-grants-1992_01
Patent number
US05081136

Reaction notes

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