3,4-Dimethylaniline → HCID 178503192, compound

Participants

Reaction Steps

To a solution of 3,4-dimethylaniline (10 g, 83 mmol) in THF (10 ml), lithium bis(trimethylsilyl)amide (20% in THF, 93 ml, 99 mmol) was added under stirring in nitrogen blanket for a period of 20 minutes followed by 4-methylthiobenzonitrile (12.31 g, 83 mmol) over a period of 10 min. After 1 hour the reaction mixture was poured over ammonium chloride solution (30%, 100 ml). The resultant mixture was extracted with ethyl acetate and washed with water, dried over anhydrous sodium sulphate. The ethyl acetate extract was concentrated to yield the title compound (19 g, yield 85.1%, mp 111-113° C., purity 99.1% by HPLC). 1H-NMR (CDCl3):δ 2.23-2.24 (d, 6H), 2.51 (s, 3H), 4.81 (bs, 2H, D2O exchangeable), 6.70-6.72 (m, 1H), 6.77 (s, 1H), 7.08-7.1 (d, 1H), 7.25-7.27 (d, 2H), 7.76-7.78 (d, 2H). MS m/z: 271.3 (M+).

Provenance & Evidence