Imidazole → HCID 13764017, compound

HRID 1982536Notes

Reaction equation

HRID 1982536 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([CH:11]2[CH2:13][CH2:12]2)=O)[CH:6]=[CH:7][CH:8]=1.[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:15]3[N:14]([CH:18]=[CH:17][N:16]=3)[CH2:12][CH2:13][CH:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 12634433Cyclopropyl(3-methoxyphenyl)methanone

Product 1

HCID 13764017HCID 13764017, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 35 g of crude cyclopropyl 3-methoxyphenyl ketone with 60 g of imidazole, and heat to 200° C. for 18 hr. Dissolve the reaction mixture in 500 ml of methylene chloride, and wash with three 300 ml portions of water to remove the excess imidazole, further wash with two 100 ml portions of 10% sodium hydroxide. Dry the methylene chloride portion over magnesium sulfate, and remove the solvent in vacuo. Crystallize the residue from ether to provide the title compound.

Workup

  1. washwash with three 300 ml portions of water
  2. customto remove the excess imidazole
  3. washfurther wash with two 100 ml portions of 10% sodium hydroxide
  4. dry with materialDry the methylene chloride portion over magnesium sulfate
  5. customremove the solvent in vacuo
  6. customCrystallize the residue from ether

Sources & evidence

ORD record
ord-73033ef090a04ddb8a135864fb5a072e
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

Loading…