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

HRID 637594Notes

Reaction equation

HRID 637594 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.C1C=CC=CC=1.[N+:31]([C:34]1[CH:41]=[CH:40][C:37]([CH2:38]Cl)=[CH:36][CH:35]=1)([O-:33])=[O:32]>CN(C)C=O>[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][CH2:38][C:37]1[CH:40]=[CH:41][C:34]([N+:31]([O-:33])=[O:32])=[CH:35][CH:36]=1)=[O:5]

Participants

6

Reactant 4

HCID 241BenzeneHCID 74824-Nitrobenzyl chlorideHCID 8471TriethylamineHCID 178481842HCID 178481842, compound

Product 1

HCID 133217144-(2,4-Dichlorobenzoyl)-1-methyl-5-(4-nitrobenzyloxy)-pyrazoleYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.36 g (0.005 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, 0.51 g (0.005 mol) of triethylamine, 20 ml of benzene and 10 ml of N,N-dimethylformamide was added with stirring 0.86 g (0.005 mol) of 4-nitrobenzyl chloride at room temperature. The resulting mixture was then heated under reflux for 3 hours. After cooling the reaction mixture, the solvent was distilled off under reduced pressure and 30 ml of water and 30 ml of ethyl acetate were added thereto. After stirring the mixture for a while, an organic layer was separated, washed with water and 5% aqueous sodium bicarbonate and dried. Then the solvent was distilled off therefrom. The resulting oil (2.02 g) was subjected to column chromatography (silica gel, eluting with benzene/ethyl acetate 1:1) to give 1.76 g of the title compound (yield 87%), m.p. 116.5°-117.5° C.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was then heated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling the reaction mixture
  5. distillationthe solvent was distilled off under reduced pressure and 30 ml of water and 30 ml of ethyl acetate
  6. additionwere added
  7. customan organic layer was separated
  8. washwashed with water and 5% aqueous sodium bicarbonate
  9. customdried
  10. distillationThen the solvent was distilled off
  11. washThe resulting oil (2.02 g) was subjected to column chromatography (silica gel, eluting with benzene/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b13b5f09537d469397b70e647603b5f8
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

Loading…