N,N-dimethyl-3-(trifluoromethyl)aniline → HCID 86745106, compound

Participants

Reaction Steps

A mixture of 8.21 g (43.4 mmol) 3-(trifluoromethyl)-N,N-dimethylaniline and8.43 g (45.3 mmol) methyl p-toluenesulfonate (methyl tosylate) was mixed and heated to 80°±10° C. for 1.5 hr. The mixture was cooled and treated with ether, resulting in a suspension of fine powdery crystals. These were collected by filtration, washed with ether, and driedin a vacuum oven: 7.51 g (46.1%). The product was identified as 3-(trifluoromethyl)-N,N,N-trimethylanilinium tosylate by 1H NMR, IR,MS, and combustion analysis. Concentration of the filtrate yielded an additional 2.44 g (15.0%). The combined product was further purified by recrystallization from ethanol/toluene: mp 176.0°-178.2° C.; 1H NMR (CDCl3): δ 2.31 (s, 3H), 3.90 (s, 9H), 7.33 (aa`mm`, 4H), 7.59 (m 2H), 7.95 (m, 1H), and 8.40 ppm (m, 2H); IR (KBr): ν 1322, 1199, 1127, 812, and 689 cm-1 ; FDMS: m/e 204 amu (R4N+); anal. calcd. for C17H20F3NO3 (375.41): 3.7% N, 54.4% C, 5.4% H, and 15.2% F; found: 4.2, 4.6% N, 54.3, 54.4% C, 5.4, 5.7% H, and 15.3% F.

Provenance & Evidence