Hydrochloric Acid → 4-[1-(1-Imidazolyl)-butyl]-benzoic acid cyclohexyl ester

HRID 727854Notes

Reaction equation

HRID 727854 reaction equation
[N:1]1([CH:6]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:19]1(O)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.N1C=CC=CC=1.Cl>C(Cl)Cl>[CH:19]1([O:15][C:14](=[O:16])[C:13]2[CH:17]=[CH:18][C:10]([CH:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[CH2:7][CH2:8][CH3:9])=[CH:11][CH:12]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7966CyclohexanolHCID 145143684-[1-(1-Imidazolyl)-butyl]-benzoic acid

Product 1

HCID 541855554-[1-(1-Imidazolyl)-butyl]-benzoic acid cyclohexyl esterYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 g of 4-[1-(1-imidazolyl)-butyl]-benzoic acid is converted, analogously to example 20, into the acid chloride; it is dissolved in 10 ml of methylene chloride, mixed with 360 mg of cyclohexanol and 3 ml of pyridine, after 20 hours at room temperature it is added to excess 1M hydrochloric acid and extracted with ether. The water phase is alkalized with potassium carbonate and extracted with ethyl acetate. After drying and concentration by evaporation, the residue is distilled on a bulb tube. 915 mg of the title compound is obtained as oil with a boiling point of 200° C./0.03 mbar.

Workup

  1. extractionextracted with ether
  2. extractionextracted with ethyl acetate
  3. customAfter drying
  4. concentrationconcentration
  5. customby evaporation
  6. distillationthe residue is distilled on a bulb tube

Sources & evidence

ORD record
ord-84c8a2d813d8415892ee96a287f42d37
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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