Pyrazole → 1-(2,4,6-Trichlorophenyl)-3-acetylamino-4-pyrazolyl-5-oxo-2pyrazoline

HRID 1708854Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13](Br)[C:12]([NH:17][C:18](=[O:20])[CH3:19])=[N:11]1.[NH:21]1[CH:25]=[CH:24][CH:23]=[N:22]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([C:25]2[CH:24]=[CH:23][NH:22][N:21]=2)[C:12]([NH:17][C:18](=[O:20])[CH3:19])=[N:11]1

Participants

Conditions

Temperature: 75 °C

Procedure

Next, 57 g (0.15 mol) of the 1-(2,4,6-trichlorophenyl)-3-acetylamino-4-bromo-5-oxo-2-pyrazoline and 41 g of pyrazole (0.6 mol) were mixed well, then heated for 6 hours at 75° C. in a stream of nitrogen gas to react, after which the reaction mixture was cooled to room temperature. Next the reaction mixture was dissolved in ethyl acetate and the solution was washed with water three times and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, acetonitrile was added to the residual oil, and the deposited crystals were filtered to obtain 20.1 g (34.7%) of 1-(2,4,6-trichlorophenyl)-3-acetylamino-4-pyrazolyl-5-oxo-2pyrazoline.

Workup

customto react
temperatureafter which the reaction mixture was cooled to room temperature
washthe solution was washed with water three times
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off under reduced pressure, acetonitrile
additionwas added to the residual oil
filtrationthe deposited crystals were filtered

Sources & evidence

ORD record: ord-46a980f9805a405f9046d2dc1a11c967
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04946771

Reaction notes

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