Imidazole → HCID 18961004, compound

HRID 1708139Notes

Reaction equation

HRID 1708139 reaction equation
C(O)CC.Cl[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1.[NH:18]1[CH:22]=[CH:21][N:20]=[CH:19]1>O>[N:18]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10311-PropanolHCID 12685614HCID 12685614, compound

Product 1

HCID 18961004HCID 18961004, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 30 ml of n-propanol, there were added 2.695 g of 4-(3-chloropropoxy)benzonitrile and 10.21 g of imidazole and the resulting mixture was heated under reflux for 24 hours. After concentration of the reaction mixture, water was added to the residue obtained, followed by extraction with chloroform, washing of the resulting extract with water and then drying the same. After concentration of the extract, the residue obtained was recrystallized from a mixture of ether and n-hexane, followed by addition of n-hexane, filtration and drying to give 2.575 g (yield 75.3%) of 4-[3-(1H-imidazolyl)propoxy]benzonitrile having a melting point of 60.0°-61.5° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 24 hours
  3. customobtained
  4. extractionfollowed by extraction with chloroform
  5. washwashing of the resulting
  6. extractionextract with water
  7. customdrying the same
  8. customAfter concentration of the extract, the residue obtained
  9. customwas recrystallized from a mixture of ether and n-hexane
  10. additionfollowed by addition of n-hexane, filtration
  11. customdrying

Sources & evidence

ORD record
ord-068195802a6c4e51ab0ac0d06e2940c5
Source dataset
uspto-grants-1994_10
Patent number
US05356916

Reaction notes

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