Water → HCID 20567236, compound

HRID 847718Notes

Reaction equation

HRID 847718 reaction equation
[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>N1C=CC=CC=1>[C:20]([O:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH2:3][CH2:4][N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 12698956HCID 12698956, compound

Product 1

HCID 20567236HCID 20567236, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.26 g 1-[3-hydroxy-3-(2-naphthyl)-n-propyl]imidazole in 20 ml 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-[3-benzoyloxy-3-(2-naphthyl)-n-propyl]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. extractionextracted with ethyl acetate
  2. washthe extracts washed
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customto remove residual pyridine

Sources & evidence

ORD record
ord-fe28f0008a0e4f5ba4e752f6eb3040b8
Source dataset
uspto-grants-1981_10
Patent number
US04293561

Reaction notes

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