Phosphorus oxychloride → 5-(4-chloro phenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile

HRID 254822Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH2:23])=O)[C:9]=2[CH3:24])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]#[N:23])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Added dropwise to a solution of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide (1.57 g, 4.1 mmol) obtained in Step 1 dissolved in dimethylformamide (10 ml) at 0° C., was phosphoryl chloride (0.72 ml, 8.2 mmol). The resulting mixture was stirred for 20 minutes at 0° C. and then stirred for 1 hour at room temperature. The reaction mixture was quenched with water at 0° C., and an mixture was extracted with ethyl acetate (30 ml twice). After removing the solvent, 5-(4-chloro phenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile was obtained by column chromatography as white solid (1.47 g, quantativly).

Workup

stirringstirred for 1 hour at room temperature
customThe reaction mixture was quenched with water at 0° C.
extractionan mixture was extracted with ethyl acetate (30 ml twice)
customAfter removing the solvent

Sources & evidence

ORD record: ord-292a9599d8e044839de0bedff5959fbe
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875647B2

Reaction notes

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