Water → 1H-Pyrrole-3-carbonitrile, 2-(4-chlorophenyl)-4,5-bis(trifluoromethyl)-

HRID 974406Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=O)O[C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[CH:4][CH:3]=1.Br/C(=[CH:22]\[C:23]([F:26])([F:25])[F:24])/C#N.[CH2:27]([N:29](CC)CC)C.O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[C:22]([C:23]([F:26])([F:25])[F:24])[C:12]=2[C:27]#[N:29])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

4-(p-Chlorophenyl)-2-(trifluoromethyl)-2-oxazolin-5-one (2.0 g, 7.59 mmol) and 2-bromo-4,4,4-trifluorocrotononitrile (0.81 g, 4.05 mmol) are dissolved in acetonitrile (10 mL). To the resulting yellow solution triethylamine (0.45 g, 4.46 mmol) is added dropwise while the reaction flask is cooled with a water bath. After stirring at 25° C. overnight, the reaction mixture is poured into water. The aqueous layer is extracted with ethyl acetate and the combined organic extracts are washed sequentially with water, 5% sodium thiosulfate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. The solid is chromatographed using silica gel and eluted with hexane/ethyl acetate 3:1 to yield the title compound as yellow crystals (1.26 g, mp 208° C.)

Workup

temperatureis cooled with a water bath
extractionThe aqueous layer is extracted with ethyl acetate
washthe combined organic extracts are washed sequentially with water, 5% sodium thiosulfate solution and brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated in vacuo
customto give a yellow solid
customThe solid is chromatographed
washeluted with hexane/ethyl acetate 3:1

Sources & evidence

ORD record: ord-74fd8a50111f4d2f955966fba0b3d870
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068390

Reaction notes

Loading…