Benzoyl chloride → HCID 20475920, compound

HRID 1277430Notes

Reaction equation

HRID 1277430 reaction equation
[OH:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:19])[CH:15]=2)[CH:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>N1C=CC=CC=1>[C:20]([O:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:19])[CH:15]=2)[CH:10]=1)[CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[CH:5]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 20475913HCID 20475913, compound

Product 1

HCID 20475920HCID 20475920, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.26 g. 1-[2-hydroxy-2-(6-methyl-2-naphthyl)ethyl]imidazole in 20 ml. pyridine is treated dropwise with stirring with 0.72 ml. of benzoyl chloride and the mixture stirred overnight. The resulting solutionis poured into 100 ml. water, extracted with ethyl acetate and the extractswashed, dried (MgSO4) and evaporated in vacuo to remove residual pyridine and afford 1-[2-benzoyloxy-2-(6-methyl-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 the hydrochloride salt.

Workup

  1. additionThe resulting solutionis poured into 100 ml
  2. extractionwater, extracted with ethyl acetate
  3. dry with materialthe extractswashed, dried (MgSO4)
  4. customevaporated in vacuo
  5. customto remove residual pyridine

Sources & evidence

ORD record
ord-c9c13bbc4b7a4c49ada5efb0be05d71c
Source dataset
uspto-grants-1981_07
Patent number
US04277486

Reaction notes

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