Methylamine → 4-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-N-methyl-5-(trifluoromethyl)pyrrole-3-thiocarboxamide

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Reaction Conditions

Reaction Steps

Isobutylchloroformate (0.3 mL, 2.3 mmol) is added to a mixture of 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylic acid (0.83 g, 2 mmol) and triethylamine (0.33 mL, 2.3 mmol) in tetrahydrofuran at 0° C. The mixture is stirred for 1 hour at 0° C., treated with a 6 wt/wt % methylamine solution (10.6 g, 20 mmol), stirred at room temperature for 2 hours and diluted with a diethyl ether/water mixture. The organic phase is separated, dried over anhydrous Na2SO4, concentrated in vacuo, diluted with toluene and concentrated in vacuo to obtain a liquid. A mixture of the liquid in tetrahydrofuran is treated with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (0.40 g, 1 mmol), heated at reflux for 2 hours, concentrated in vacuo and chromatographed on silica gel with a 4:1 hexane/ethyl acetate mixture to obtain the title product as a yellow gum (0.3 g) which is identified by 1H and 13C NMR spectral analyses.

Provenance & Evidence