Hydrochloric Acid → 1-[4-(chloromethyl)phenyl]-1H-imidazole hydrochloride

HRID 846724Notes

Reaction equation

HRID 846724 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12]O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:14].S(Cl)([Cl:17])=O>ClC(Cl)Cl>[ClH:17].[Cl:14][CH2:12][C:9]1[CH:10]=[CH:11][C:6]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 2776486(4-(1H-Imidazol-1-yl)phenyl)methanol

Product 1

HCID 197946621-[4-(chloromethyl)phenyl]-1H-imidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 11.3 parts of 4-(1H-imidazol-1-yl)benzenemethanol in 375 parts of trichloromethane was acidified with gaseous hydrogen chloride at room temperature. Then there were added dropwise 10.6 parts of thionyl chloride at room temperature. Upon completion, stirring was continued first for 30 minutes at reflux and further for 30 minutes at room temperature. The reaction mixture was evaporated. The residue was taken up a few times in methylbenzene and the latter was evaporated each time. The residue was stirred for 1 hour in 2,2'-oxybispropane. The product was filtered off, washed with 2,2'-oxybispropane and dried in vacuo overnight, yielding 13.5 parts of 1-[4-(chloromethyl)phenyl]-1H-imidazole monohydrochloride (intermediate 20).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe latter was evaporated each time
  3. stirringThe residue was stirred for 1 hour in 2,2'-oxybispropane
  4. filtrationThe product was filtered off
  5. washwashed with 2,2'-oxybispropane
  6. customdried in vacuo overnight

Sources & evidence

ORD record
ord-739a03601b9347d3acaa579afd48a05e
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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