Potassium Carbonate → 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-2-nitro-N-propylbenzenamine

HRID 2395642Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16](F)[C:15]([N+:19]([O-:21])=[O:20])=[CH:14][C:13]=2[F:22])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8].C([O-])([O-])=O.[K+].[K+].[CH3:29][NH:30][CH2:31][CH2:32][CH3:33]>CN1CCCC1=O.O>[Cl:1][C:2]1[C:3]([C:12]2[C:13]([F:22])=[CH:14][C:15]([N+:19]([O-:21])=[O:20])=[C:16]([N:30]([CH3:29])[CH2:31][CH2:32][CH3:33])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

Conditions

Temperature: 35 °C

Procedure

At 25° C., 6.83 g (0.02 mole) 4-chloro-3-(2,5-difluoro-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, 4.1 g (0.03 mole) K2CO3, 3.1 mL (0.03 mole) N-methyl-N-propylamine and a catalytic amount of CuF2 were slurried in 50 mL 1-methyl-2-pyrrolidinone. The reaction mixture was stirred at 35° C. for 2 hours. The mixture was cooled, diluted with 100 mL cold water, and extracted four times with ethyl acetate. The ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4, and stripped in vacuo. The residue was purified chromatographically using 15% ethyl acetate in hexane as the eluent to give 6.8 g (86%) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluoro-N-methyl-2-nitro-N-propylbenzeneamine as an orange oil, nD25 51.5534.

Workup

customAt 25° C.
temperatureThe mixture was cooled
extractionextracted four times with ethyl acetate
washThe ethyl acetate extracts were washed with brine
dry with materialdried over anhydrous MgSO4
customThe residue was purified chromatographically

Sources & evidence

ORD record: ord-0b2f46d7de9c411190e6b9919a31f9b5
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489571

Reaction notes

Loading…