Water → 2-(2-Phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilide

HRID 429804Notes

Reaction equation

[C:1]1([CH:7]=[CH:8]C2C=CC=CC=2N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:18]([CH2:21][CH3:22])CC)C.[F:23][CH:24]([F:34])[O:25][C:26]1[CH:30]=[CH:29][S:28][C:27]=1[C:31](Cl)=[O:32].O>C1(C)C=CC=CC=1>[C:1]1([CH:7]=[CH:8][C:27]2([C:31]([NH:18][C:21]3[CH:22]=[CH:3][CH:2]=[CH:1][CH:6]=3)=[O:32])[CH:26]([O:25][CH:24]([F:34])[F:23])[CH:30]=[CH:29][S:28]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

At room temperature, a solution of 0.3 g (0.0015 mol) of 2-(2-phenyl-ethen-1-yl)-aniline in 2 ml of toluene is admixed with a solution of 0.15 g (0.0015 mol) of triethylamine in 10 ml of toluene. At room temperature, 0.33 g (0.0015 mol) of 3-difluoromethoxy-thiophene-2-carbonyl chloride are added to this mixture with stirring. The mixture is subsequently heated to 50° C. and stirred at this temperature for 2 hours. For work-up, the reaction mixture is then cooled to room temperature and admixed with water. The organic phase is separated off, dried over sodium sulphate and then concentrated under reduced pressure at 60° C. The residue that remains is chromatographed over silica gel using diethyl ether. Concentration of the eluate gives 0.53 g (95% of theory) of 2-(2-phenyl-ethen-1-yl)-3-difluoromethoxy-thiophene-2-carboxanilide in the form of a solid substance of melting point 80 to 82° C.

Workup

customAt room temperature
stirringstirred at this temperature for 2 hours
temperatureFor work-up, the reaction mixture is then cooled to room temperature
customThe organic phase is separated off
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure at 60° C
customThe residue that remains is chromatographed over silica gel

Sources & evidence

ORD record: ord-6b559aa5e99f45c7ac2505d15179bda8
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06319940B1

Reaction notes

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