Thionyl Chloride → 1-(4-Chloromethylphenyl)-2-methyl-1H-imidazole

HRID 728941Notes

Reaction equation

HRID 728941 reaction equation
[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.S(Cl)([Cl:17])=O>>[Cl:17][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 11735617[4-(2-Methylimidazol-1-yl)phenyl]methanol

Product 1

HCID 149988211-(4-Chloromethylphenyl)-2-methyl-1H-imidazole

Procedure

To 4-(2-methyl-1H-imidazole-1-yl)benzenemethanol add thionyl chloride. Monitor the progress of the reaction by thin-layer chromatography. Upon completion remove the excess thionyl chloride in vacuo. Partition the residue between 1N NaOH and CH2Cl2. Separate and dry the organic layer. Remove the solvent in vacuo to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customUpon completion remove the excess thionyl chloride in vacuo
  3. customPartition the residue between 1N NaOH and CH2Cl2
  4. customSeparate
  5. customdry the organic layer
  6. customRemove the solvent in vacuo

Sources & evidence

ORD record
ord-245439cab45d4f77bb5fbb28c73a2f97
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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