Benzoyl chloride → 2,6-Diethyl-4-nitrophenylthiourea

Participants

Reaction Steps

To 2.34 g (24.1 mmol) of potassium thiocyanate in 30 ml of acetone was added 2.32 ml (20.0 mmol) of benzoyl chloride. The mixture was then refluxed for 15 min, cooled to r.t., and 3.16 g (16.3 mmol) of 2,6-diethyl-4-nitroaniline obtained from step C was added. The mixture was then refluxed for 15 min, cooled to r.t., and poured into 200 ml of ice-water. The precipitate was collected and washed with water, then dissolved in a solution comprising 0.70 g (18 mmol) of sodium hydroxide in 5 ml of water and 50 ml of ethanol. The solution was refluxed for 1 hr, cooled to r.t., poured into icewater, then the precipitate was collected, washed with water several times, and dried. The solids were then triturated with ethyl acetate to yield 2.44 g (59.2%) of product. NMR (CDCl3, d6 -DMSO):δ 1.30 (t, 6H), 2.74 (q, 4H), 6.9 (b, 2H), 7.98 (s, 2H), 9 (b, 1H).

Provenance & Evidence