Benzoyl chloride → 1-[2-Benzoyloxy-2(2-naphthyl)ethyl]imidazole

HRID 26541Notes

Reaction equation

HRID 26541 reaction equation
[OH:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:19]([O:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 130368alpha-2-Naphthalenyl-1H-imidazole-1-ethanol

Product 1

HCID 126989691-[2-Benzoyloxy-2(2-naphthyl)ethyl]imidazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.19 g. 1-[2-hydroxy-2-(2-naphthyl)ethyl]imidazole in 20 ml. of pyridine is treated dropwise with stirring with 0.72 ml. of benzoyl chloride and the mixture stirred overnight. The resulting solution is poured into 100 ml. water, extracted with ethyl acetate and the extracts washed, dried (MgSO4) and evaporated in vacuo to remove residual pyridine and afford 1-[2-benzoyloxy-2(2-naphthyl)ethyl]imidazole. The residue is dissolved in ether, treated with ethereal hydrogen chloride and the resulting precipitate recrystallized from acetone/methanol to give 1.3 g. of hydrochloride salt, m.p. 219°-219.5° C.

Workup

  1. additionThe resulting solution is poured into 100 ml
  2. extractionwater, extracted with ethyl acetate
  3. washthe extracts washed
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto remove residual pyridine

Sources & evidence

ORD record
ord-4977e13834434f91abb11fb59d6540b8
Source dataset
uspto-grants-1979_04
Patent number
US04150153

Reaction notes

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