Cyclobutylamine → 3-(Benzo[1,3]dioxol-5-ylamino)-3-cyclobutylamino-2-(4-chlorophenylsulfonyl)-propenenitrile

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Reaction Steps

3-(Benzo[1,3]dioxol-5-ylamino-2-(4-chloro-phenylsulfonyl)-3-methylsulfanyl-2-propenenitrile (0.29 g, 0.7 mmol) was stirred in cyclobutylamine (0.6 ml 7.0 mmol) for 17 h at 100° C. under nitrogen in a sealed flask. The reaction mixture was concentrated and the residue was crystallised from ethyl acetate to give 88 mg (29%) of the title compound. Mp 189.5° C. 1H NMR (200 MHz, CDCl3): δ=1.6 (m, 2H), 1.75 (m, 2H), 2.05 (m, 2H), 3.80 (m, 1H), 6.02 (s, 2H), 6.5 (m, 2H), 6.79 (d, 2H), 7.50 (dt, 2H), 7.83 (dt, 2H). Analysis: calc. for C20H18ClN3O4S: C, 55.62%; H, 4.20%; N, 9.73%; Found: C, 55.59%; H, 4.21%; N, 9.59%.

Provenance & Evidence