Thionyl Chloride → 1-benzyl-3-(chloromethyl)-5-methoxy-1H-indazole

HRID 76114Notes

Reaction equation

HRID 76114 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19]O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][Cl:23])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 44217645HCID 44217645, compound

Product 1

HCID 668465571-benzyl-3-(chloromethyl)-5-methoxy-1H-indazoleYield 47.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (1-benzyl-5-methoxy-1H-indazol-3-yl)methanol (18 g; 0.07 mol) in chloroform (200 ml) stirred at room temperature was slowly added thionyl chloride (15.8 g; 0.13 mol). Once the addition was complete, the solution was refluxed for 24 hours. The reaction was then stopped by cooling the mixture to room temperature and evaporating off the solvent under reduced pressure. The residue was then taken up several times in toluene and concentrated under reduced pressure. The crude residue obtained was purified by crystallization from hexane to give 9.5 g of 1-benzyl-3-(chloromethyl)-5-methoxy-1H-indazole with a melting point of 78-80° C.

Workup

  1. additionOnce the addition
  2. temperaturethe solution was refluxed for 24 hours
  3. customevaporating off the solvent under reduced pressure
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue obtained
  6. customwas purified by crystallization from hexane

Sources & evidence

ORD record
ord-775b3faa84af413f9e5bf5b98780b87a
Source dataset
uspto-grants-2014_09
Patent number
US08835481B2

Reaction notes

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