2,4,6-Trimethylaniline → HCID 11785596, compound

Participants

Reaction Steps

[4-(2-Chloro-6-methylpyridine-3-sulfonyl)-phenyl]-methanol (1.15 g, 3.86 mmol) and 2,4,6-trimethyl aniline (3.13 g, 23.2 mmol) were heated at reflux in ethylene glycol (3.5 mL) for 16 h. After cooling the mixture was diluted with water (50 mL) and extracted with ethyl acetete (2×200 mL). The combined organic extracts were washed with brine, dried and stripped in vacuo. The residue was purified by column chromatography on silica gel (40% EtOAc/hexanes eluent) to give the product {4-[6-methyl-2-(2,4,6-trimethylphenylamino)-pyridine-3-sulfonyl]-phenyl}-methanol as an amorphous solid (836 mg, 55% yield for the two steps) and (6-methyl-3-{4-[(2,4,6-trimethylphenylamino)-methyl]-benzenesulfonyl}-pyridin-2-yl)-(2,4,6-trimethyl-phenyl)-amine (53 mg, 3.5% yield). mass spec. (AP+): m/z 397 (M+1).

Provenance & Evidence