Methyl 2-(bromomethyl)-3-nitrobenzoate → 2-[[(Amino)(imino)methyl]thiomethyl]-3-nitrobenzoic acid, methyl ester, hydrobromide

Participants

Reaction Steps

A solution of 18.8 g of the product from Example 1 and 5.2 g thiourea in 150 ml methanol was stirred at reflux temperature overnight. Removal of the solvent in vacuo yielded a viscous oil which slowly crystallized. The crude product was washed well with ethyl acetate, filtered and dried. The yield of 2-[[(amino)(imino)methyl]-3-nitrobenzoic acid, methyl ester hydrobromide, m.p. 178°-180°(dec.), was 22.6 g; NMR (CDCl3 /DMSO-d6): δ 4.0 (3H, s, CO2CH3), 4.85 (2H, s, --CH2 --), 7.6-8.35 (3H, m), 9.05 (4H, br s, NH).

Provenance & Evidence