Methyl iodide → N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

0.55 g (1 mol equiv.) 2,3-Diazaspiro[4.4]non-3-ene-2-carbothioic acid ethylamide was dissolved in 15 mL MeOH, 3.4 mL (21 mol equiv.) iodomethane was added and the magnetically stirred reaction mixture was heated at 45° C. for 2 hours. Volatiles were removed in vacuo. The residue was taken up in dichloromethane (DCM) and extracted with 5% aqueous NaHCO3. The organic layer was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness to give 0.57 g (97%) N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.3 Hz, 3H), 1.64-1.80 (m, 8H), 2.46 (s, 3H), 3.54 (q, J=7.3 Hz, 2H), 3.57 (s, 2H), 6.72 (s, 1H).

Provenance & Evidence