2,6-Lutidine → 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [1-fluoromethyl-2-(2,4,6-trichlorophenyl)-ethyl]-methoxy-amide

HRID 1039344Notes

Reaction equation

[F:1][CH2:2][CH:3]([NH:14][O:15][CH3:16])[CH2:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:6]=1[Cl:13].N1C(C)=CC=CC=1C.[F:25][C:26]1[N:30]([CH3:31])[N:29]=[C:28]([CH3:32])[C:27]=1[C:33](F)=[O:34]>ClC1C=CC=CC=1.ClCCl>[F:1][CH2:2][CH:3]([N:14]([O:15][CH3:16])[C:33]([C:27]1[C:28]([CH3:32])=[N:29][N:30]([CH3:31])[C:26]=1[F:25])=[O:34])[CH2:4][C:5]1[C:6]([Cl:13])=[CH:7][C:8]([Cl:12])=[CH:9][C:10]=1[Cl:11]

Participants

Conditions

Temperature: 130 °C

Procedure

To a stirred solution of N-[1-fluoromethyl-2-(2,4,6-trichloro-phenyl)-ethyl]-O-methylhydroxylamine (0.20 g; 0.70 mmol), prepared as described in example P6f2 in chlorobenzene (3.8 ml) was added 2,6-lutidine (85 μl; 0.74 mmol) and 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl fluoride (0.11 g; 0.70 mmol). The yellow solution was stirred at reflux (130° C.) for 22 hours. The dark brown solution was dissolved in dichloromethane (20 ml), washed with 1 M sodium hydroxide solution (20 ml), 1 M hydrochloric acid solution (20 ml), brine (20 ml), dried over sodium sulfate and evaporated under reduced pressure. The crude was subject to flash chromatography (eluant: c-hexane/ethyl acetate 9:1 to 7:3) to afford 20 mg (7% of theory) of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxylic acid [1-fluoromethyl-2-(2,4,6-trichlorophenyl)-ethyl]-methoxy-amide as a brown oil.

Workup

washwashed with 1 M sodium hydroxide solution (20 ml), 1 M hydrochloric acid solution (20 ml), brine (20 ml)
dry with materialdried over sodium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-831ae32e583d4af39cf8e48fc6a6c20a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552049B2

Reaction notes

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