Thionyl Chloride → 2-(2-(chloromethyl)-4-methylphenyl)-2H-1,2,3-triazole

HRID 41593Notes

Reaction equation

HRID 41593 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[N:14]=[CH:13][CH:12]=[N:11]2)=[C:6]([CH2:8]O)[CH:7]=1.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[Cl:17][CH2:8][C:6]1[CH:7]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N:10]1[N:14]=[CH:13][CH:12]=[N:11]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 67250917(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanol

Product 1

HCID 683332752-(2-(chloromethyl)-4-methylphenyl)-2H-1,2,3-triazoleYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanol (100 mg, 0.53 mmol) in chloroform (3 mL), thionyl chloride (76 mg, 0.63 mmol) was added dropwise at 0° C. and stirred for 1 h. Then the mixture was allowed to warm to rt and stirred overnight. The reaction mixture was concentrated under reduced pressure. Saturated aqueous NaHCO3 solution (5 mL) was added and extracted with ethyl acetate (2×). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to yield the title compound (100 mg, 91%). [TLC Rf=0.59 (ethyl acetate/hexane 30:70)].

Workup

  1. stirringstirred overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionSaturated aqueous NaHCO3 solution (5 mL) was added
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9ac4934e42ee4f3cbac6848ca2e8736e
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Reaction notes

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