Water → HCID 13365750, compound

Participants

Reaction Steps

Aqueous NaOH (3.41 mL, 2 N) was added to a solution of N-[[6-methoxy-5-(trifluoromethylthio)-1-naphthalenyl]thioxomethyl]-N-methylglycine methyl ester (1.375 g, 3.4 mmoles) in 2-methoxyethanol (20 ml). The solution was stirred at 20°-22° C. for 4 hr. Water was added and the cloudy mixture was extracted with ethyl acetate. The aqueous layer was made acidic (pH=3) with 1 N aqueous HCl and extracted with ethyl acetate. The latter extract was washed successively with water and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was crystallized from chloroform-hexane to give the title compound (672 mg); mp 168°-169° C.; NMR (DMSO-d6) δ 3.0 (s, 3H), 4.0 (s, 3H), 4.6 and 5.2 (d, J=16.5 Hz, 2H), 7.7 (m, 5H); ir (white mineral oil) 2900, 1720, 1465 cm-1 ; uvλmax (MeOH) 342 nm (ε4970), 334 (4800), 230 (46,800).

Provenance & Evidence