4-[(Trifluoromethyl)thio]benzenamine

clear colorless to yellow liquid

To a solution of 4-nitrophenyl trifluoromethylsulfide (6) (33.5 g, 0.15 mol) in ethanol (400 mL) was added palladium on carbon (10 percentPd/C, 3.5 g). The mixture was hydrogenated under 40 atmospheric pressure at room temperature for 8 h. After completionof the reaction, the reaction mixture was filtered through celite and thoroughly washed with ethanol. The filtrate was evaporated and the residue washed with water to give 28.4 g in a98 percent yield of 4-aminophenyl trifluoromethylsulfide (7) as a brown liquid. b.p.: 110-112 °C/1.70 KPa (lit. [14]; b.p.:113 °C/1.73 KPa). 1H NMR (300 MHz, CDCl3), δ = 7.62 (d, J= 8.30, 2H), 7.42 (dd, J = 8.30, J = 1.90, 2H); 3.84 (s, 2H, NH2).19F NMR (220 MHz, CDCl3): δ: 44.5 (s, 3F, SCF3). 13CNMR (75 MHz, CDCl3): δ 149.1, 138.2, 126.7, 115.3, 111.3.[Protocol B]--4-(trifluoromethylthio)aniline colourless solid (EtOAc/hexane). MS (ES+): m/z (%)=473 (M+H 81 Br, 100), 471 (M+H 79 Br, 94). 1 -NMR (DMSO d6): delta=3.81 (3H, s, NCH3), 7.11 (1H, d, J=7.5, ArH), 7.47 (1H, t, J=7.9, ArH), 7.51-7.63 (6H, m, ArH), 7.66 (1H, s, ArH), 9.03 (1H, s, NH), 9.16 (1H, s, NH).[Protocol B]--4-(trifluoromethylthio)aniline colourless solid (EtOAc/hexane) MS (ES+): m/z (%)=473 (M+H 81 Br, 100), 471 (M+H 79 Br, 94). 1 H-NMR (DMSO d6): delta=3.81 (3H, s, NCH3), 7.11 (1H, d, J=7.5, ArH), 7.47 (1H, t, J=7.9, ArH), 7.51-7.63 (6H, m, ArH), 7.66 (1H, s, ArH), 9.03 (1H, s, NH), 9.16 (1H, s, NH).4-[(trifluoromethyl) sulfanyl] aniline 20g, and a mixture of chloroform 40 mL, was added dropwise acetic anhydride 20mL under ice-cooling. After the addition was complete, the chloroform 40mL was added to the mixture and stirred for 12 hours at room temperature. To the resulting reaction mixture was added hexane 80 mL, the precipitated solid was filtered and washed resulting solid with hexane, described below N- {4 - [(trifluoromethyl) sulfanyl] phenyl} acetamide It was obtained 23g.(1) To a mixture of 4 - [(trifluoromethyl) sulfanyl] aniline 20 g, and chloroform 40 mL, 20 mL of acetic anhydride was added dropwise under ice cooling. After completion of dripping, Chloroform (40 mL) was added to the mixture, And the mixture was stirred at room temperature for 12 hours. To the obtained reaction mixture, 80 mL of hexane was added, the precipitated solid was filtered, By washing the obtained solid with hexane, 23 g of intermediate 8 described below was obtained.

Molecular Weight:193.19
XLogP3:3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:193.01730486
Monoisotopic Mass:193.01730486
Topological Polar Surface Area:51.3
Heavy Atom Count:12
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes