Acetic Acid → HCID 15035849, compound

Participants

Reaction Steps

A 100 mL, three-necked, round-bottomed flask was equipped with a magnetic stirrer, a heating mantle, a standard condenser with a N2 inlet, and two glass stoppers. A mixture containing 3-iodobenzylamine (1.19 g, 5.10 mmol), paraformaldehyde (1.22 g, 40.8 mmol), and CH3OH (30 mL) was made acidic with glacial acetic acid (0.46 g, 7.65 mmol). In one portion, 4-thianone (44, 0.59 g, 5.10 mmol) was added and the resulting mixture was heated under N2 at reflux for 21 h. Evaporation of the solvent gave a reddish oil, which was dissolved in H2O (40 mL). Basification (pH~13) of the solution by the dropwise addition of 10% NaOH resulted in the formation of a milky suspension which was extracted with ether (5×40 mL). Combined extracts were dried (Na2SO4, overnight), filtered, and concentrated to a yellow oil. Digestion of the oil occurred in Skelly B (125 mL, bp 60°-68° C.) for 30 min, and the supernatant was decanted. Further digestion of the residual material was effected in pentane (2×125 mL) for 30 min. Combined supernatant extracts were concentrated (rotary evaporator the vacuum pump, overnight, RT/0.2 mm Hg) to give 0.84 g (57.5%) of a slightly crude viscous oil (25) which was used without further purification in the next step. IR (film) cm-1 3055 (Ar C--H), 2930, 2825 (C--H), 1735 (C=O), 885, 790, 695 (C--H out of plane, meta); 1H NMR (DCCl3) δ2.72-3.18 [m, 10 H, ring protons and H(1,5)], 3.51 (s, 2 H, ArCH2), 7.07-7.71 (m, 4 H, Ar--H); 13C NMR (DCCl3) ppm 35.05 [C(2,4)], 46.95 [C(1,5)], 58.20 [C(6,8)], 60.69 (ArCH2), 94.43, 127.98, 130.23, 136.44, 137.64, 140.63 (Ar--C), 213.00 (C=O).

Provenance & Evidence