2-Oxopropanethioamide → 7'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazole]-4''(3''H)-thione

Participants

Reaction Conditions

Reaction Steps

7′-Bromo-3′,4′-dihydro-1′H-spiro[cyclopropane-1,2′-naphthalen]-1′-imine (Intermediate 11, 717 mg, 2.87 mmol) and 2-oxopropanethioamide (970 mg, 9.40 mmol) were dissolved in dry MeOH (25 mL) and heated at 60° C. under argon for 24 h. After standing at r.t. overnight the formed precipitate was filtered and washed with MeOH. Drying in vacuo afforded the title compound (688 mg, 65% yield). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.27-0.35 (m, 1 H), 0.35-0.45 (m, 2 H), 0.47-0.53 (m, 1 H), 1.69-1.79 (m, 1 H), 2.03-2.12 (m, 1 H), 2.27 (s, 3 H), 2.90 (t, 2 H), 6.73 (d, 1 H), 7.24 (d, 1 H), 7.47 (dd, 1 H), 12.28 (s, 1 H); MS (ES+) m/z 335.0 [M+H]+.

Provenance & Evidence