Benzene → 4-(2,4-Dichlorobenzoyl)-1-methyl-5-(p-acetylbenzyloxy)pyrazole

HRID 637595

Reaction equation

HRID 637595 reaction equation
C1C=CC=CC=1.[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:18])[C:16]=1[OH:17])=[O:11].[C:24]([C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Br)=[CH:29][CH:28]=1)(=[O:26])[CH3:25]>C(N(CC)CC)C>[Cl:7][C:8]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:9]=1[C:10]([C:12]1[CH:13]=[N:14][N:15]([CH3:18])[C:16]=1[O:17][CH2:31][C:30]1[CH:33]=[CH:34][C:27]([C:24](=[O:26])[CH3:25])=[CH:28][CH:29]=1)=[O:11]

Participants

5

Reactant 3

HCID 241BenzeneHCID 5837851-[4-(Bromomethyl)phenyl]ethan-1-oneHCID 178481842HCID 178481842, compound

Product 1

HCID 155907284-(2,4-Dichlorobenzoyl)-1-methyl-5-(p-acetylbenzyloxy)pyrazoleYield 83%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In 30 ml of dry benzene containing 0.50 g (0.005 mol) of triethylamine was dissolved 1.36 (0.005 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, and then 1.07 g (0.005 mol) of p-acetylbenzylbromide was added thereto. The resulting mixture was heated under reflux for 3 hours. After cooling the reaction mixture, the salt precipitated was filtered off and the solvent was distilled off therefrom under reduced pressure. The resulting oil was purified through column chromatography on silica gel using benzene/ethyl acetate 8:1 as an eluent to give 1.67 g of the title compound (yield 83%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling the reaction mixture
  4. customthe salt precipitated
  5. filtrationwas filtered off
  6. distillationthe solvent was distilled off
  7. customThe resulting oil was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-70c3c8650efc4dc0acd3abc0a8cb70b0
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Linked notes

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