Thionyl Chloride → 2H-1,2,3-Triazole, 2-[4-(chloromethyl)phenyl]-

HRID 2216659Notes

Reaction equation

HRID 2216659 reaction equation
[N:1]1[N:2]([C:6]2[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.S(Cl)([Cl:16])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:16][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:2]2[N:3]=[CH:4][CH:5]=[N:1]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 219436964-(2H-1,2,3-Triazol-2-yl)benzenemethanol

Product 1

HCID 219436922H-1,2,3-Triazole, 2-[4-(chloromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 50.58 g (289 mmol) of (4-[1,2,3]triazol-2-yl-phenyl)-methanol in 2000 ml of CH2Cl2, 31.59 ml (433 mmol) of thionyl chloride is added dropwise at 0–5° C. and the reaction mixture is allowed to warm to r.t. After stirring for 16 h, the reaction mixture is basified with sat. NaHCO3 at 0–5° C. and extracted with CH2Cl2. The combined extracts are washed with brine, dried over MgSO4 and concentrated under reduced pressure to provide the title compound.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-834e58427fc7400bbc3830cc5ccb4ceb
Source dataset
uspto-grants-2006_09
Patent number
US07112611B2

Reaction notes

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