Triethylamine → 4-(2,4-Dichlorobenzoyl)-1-methyl-5-(2-chlorobenzyloxy)-pyrazole

HRID 637599Notes

Reaction equation

HRID 637599 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[OH:11])=[O:5].C(N(CC)CC)C.CS(O[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:37])(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[O:11][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[Cl:37])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20255346o-Chlorobenzyl methanesulfonateHCID 178481842HCID 178481842, compound

Product 1

HCID 133217164-(2,4-Dichlorobenzoyl)-1-methyl-5-(2-chlorobenzyloxy)-pyrazoleYield 77.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 1.33 g (0.0049 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, 0.54 g (0.0054 mol) of triethylamine and 30 ml of toluene was added 1.3 g (0.0059 mol) of o-chlorobenzyl methanesulfonate. Then, the reaction mixture was refluxed with stirring for 2 hours. After cooling, the reaction mixture was washed with 20 ml of water three times, and the organic layer was separated. After drying over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure and was subjected to a column chromatography (silica gel, eluent; ethyl acetate:benzene=1:9) to obtain 1.5 g of the title compound (yield: 77%).

Workup

  1. temperatureThen, the reaction mixture was refluxed
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with 20 ml of water three times
  4. customthe organic layer was separated
  5. dry with materialAfter drying over anhydrous sodium sulfate
  6. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-43f42231fe0c4fca82740b131934f7da
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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