Hydrochloric Acid → HCID 13672317, compound

Participants

Reaction Conditions

Reaction Steps

The N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine, methyl ester (2.3 g, 5.46 mmol), 2-methoxyethanol (50 ml) and 2N aqueous sodium hydroxide (5.46 ml) were mixed at 0° C. and the mixture stirred at room temperature for 3 hours (until disappearance of the ester spot in t.l.c. with ethyl acetate/hexane 1:1). The mixture was cooled to 0° C., neutralized to pH 8 with 1N aqueous hydrochloric acid, evaporated, the residue triturated with water, the neutral material extracted with ethyl acetate and the aqueous layer acidified with 1N aqueous hydrochloric acid to pH3. The product was extracted with ethyl acetate, the extract washed with water, dried over anhydrous MgSO4 and evaporated. The residue was purified by crystallization from chloroform/hexane to obtain 700 mg of the first crop and an additional 568 mg of the crude material from the mother liquor. Recrystallization of the first crop afforded 400 mg of the pure N-[[6-methoxy-5-(pentafluoroethyl)-1-naphthalenyl]thioxomethyl]-N-methylglycine. The recrystallization of mother liquor gave further 291 mg. mp. 164°-165° C. Anal. Calcd: C, 50.13% H, 3.46% N, 3.44% Found: C, 49.42%, H, 3.58% N, 3.40%. nmr (DMSO): δ2.95 (s, 3H, N--CH3); δ3.97 (s, 3H, OCH3); δ4.9 (q, 2H, CH2); δ7.1-8.4 (m, 5H, Har). ir (nujol): 1700, 1723, 1750 cm-1 uv, λmax(ε): 338 (3990), 269 (13,000), 227 (45,400) ms: m/e 407 (M+), 363, 319.

Provenance & Evidence