2-Butanamine, 3,3-dimethyl- → 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile

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Reaction Steps

3-(3,5-Bis(trifluoromethyl)phenylamino)-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.300 g, 0.6 mmol) was stirred in 1,2,2-trimethylpropylamine (1 ml) for 19 h at 75° C. under nitrogen. The reaction mixture was concentrated and the residue dissolved in DCM, washed twice with 1N aqueous HCl and once with water. The organic phase was dried (sodium sulfate) and concentrated. The residue was crystallised from ethyl acetate/heptane 1:3 to give 225 mg (68%) of the title compound. Mp 155.5-158.5° C. 1H NMR (300 MHz, CDCl3): δ=0.9 (s, 9H), 1.0 (d, 3H), 3.0 (m, 1H), 7.40 (s, 2H), 7.50 (d, 2H), 7.70 (s, 1H), 7.82 (d, 2H); MA calc for C23H22ClF6N3O2S: C, 49.87%; H, 4.00%; N, 7.59%. Found: C, 49.86%; H, 4.29%, N, 7.55%.

Provenance & Evidence