Thionyl Chloride → HCID 19744543, compound

HRID 2242361Notes

Reaction equation

HRID 2242361 reaction equation
S(Cl)([Cl:3])=O.[N:5]1([C:10]2[CH:11]=[C:12]([CH2:16]O)[CH:13]=[CH:14][CH:15]=2)[CH:9]=[CH:8][N:7]=[CH:6]1>CN(C=O)C>[Cl:3][CH2:16][C:12]1[CH:11]=[C:10]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 197444983-(1H-Imidazol-1-yl)benzenemethanol

Product 1

HCID 19744543HCID 19744543, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (4.0 ml, 54.0 mmol) was added to a solution of (3-imidazol-1-yl-phenyl)-methanol (3.17 g, 17.0 mmol) in DMF (50 ml) and the reaction stirred at room temperature for 40 h. The solvent was evaporated, the residue diluted with DCM and washed with water, neutralised with aqueous sodium bicarbonate (pH 9-10) and then extracted with DCM (3×). The organic phase was dried over sodium sulfate, filtered and concentrated to give 1-(3-chloromethyl-phenyl)-1H-imidazole as an orange oil (5.3 g, crude contaminated with DMF).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with DCM
  3. washwashed with water
  4. extractionextracted with DCM (3×)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a6cc3b32698a402ab41ee8462d5c99e9
Source dataset
uspto-grants-2010_03
Patent number
US07671080B2

Reaction notes

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