Chloromethyl ethyl ether → HCID 66788185, compound

Participants

Reaction Steps

To a mixture of 7-(5-chloro-2-trifluoromethyl-phenyl)-6,6-dioxo-5,6-dihydro-6-thia-1,4-diaza-naphthalen-8-ol (Compound C7 of Table C) (0.54 g) and N,N-diisopropylethylamine (0.25 ml) in N,N-dimethylformamide (5 ml) under nitrogen atmosphere was added chloromethyl ethyl ether (0.20 ml) and the reaction mixture was stirred at ambient temperature. After 2 hr further diisopropylethylamine (0.10 ml) and chloromethyl ethyl ether (0.10 ml) were added. After a further 3 hours stirring the reaction was concentrated and the residue purified by chromatography on silica gel (eluent: 0-100% v/v ethyl acetate in hexane) to give 7-(5-chloro-2-trifluoromethyl-phenyl)-8-ethoxymethoxy-5H-6-thia-1,4-diaza-naphthalene 6,6-dioxide (0.276 g) 1H-NMR (400 MHz, CDCl3): 1.04 (3H, t), 3.25-3.41 (2H, m), 4.76-4.87 (2H, q), 5.13 (1H, d), 5.33 (1H, d), 7.58-7.61 (2H, m), 7.76 (1H, d), 8.62 (1H, d), 8.73 (1H, d).

Provenance & Evidence