Dimethylamine → 3-Chloro-2-(4-chloro-3-dimethylaminocarbonylphenyl)-5-trifluoromethylpyridine

HRID 1957269Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19](Cl)=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:22][NH:23][CH3:24]>C(Cl)Cl.O>[Cl:1][C:2]1[C:3]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([N:23]([CH3:24])[CH3:22])=[O:20])[CH:13]=2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3.5 g of 3-chloro-2-(4-chloro-3-chloroformylphenyl)-5-trifluoromethylpyridine in 10 ml of methylene chloride was added dropwise to 75 ml of a 40% by weight aqueous dimethylamine solution cooled to 0° C. The mixture was stirred at 0 to 5° C. for 4 hours and then diluted with 225 ml of water, after which it was extracted three times with 100 ml of tert-butyl methyl ether each time. The combined organic phases were washed twice with 100 ml of water each time, dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with cyclohexane/ethyl acetate (7:3). Yield: 2.2 g (61%) of colorless crystals; melting point: 90°-91° C.

Workup

extractionafter which it was extracted three times with 100 ml of tert-butyl methyl ether each time
washThe combined organic phases were washed twice with 100 ml of water each time
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was chromatographed on silica gel with cyclohexane/ethyl acetate (7:3)

Sources & evidence

ORD record: ord-ec923dc251594871886364faa844b686
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05783522

Reaction notes

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