Acetone → HCID 57428842, compound

Participants

Reaction Steps

A solution of 3.8 g (50 mmol) of ammonium thiocyanate in 100 mL of acetone was treated with a solution of 8.4 g (45 mmol) of 4-nitrobenzoyl chloride in 50 mL of acetone and the reaction solution was heated at reflux for 15 min. The reaction solution was removed from heating and 5.2 g (41 mmol) of 4-fluoro-N-methylaniline was added at such a rate as to maintain reflux, then heating was renewed for 15 min. The reaction mixture was poured onto 400 g of ice to give an orange oil that separated and solidified on standing. The solid was collected by filtration, washed with water and dried to give 1-(4-fluorophenyl)-1-methyl-3-(4-nitrobenzoyl)thiourea which was suspended in 500 mL of MeOH and treated with 2 mL (64 mmol) of hydrazine for 18 h. The byproduct 4-nitrobenzohydrazide was removed by filtration and the organic solvent was removed from the product in vacuo. The residue was dissolved in 500 mL of 8:1:1 (v/v/v) EtOAc/CHCl3/MeOH, washed thrice with 10% (w/v) aqueous HCl, then dried over a mixture of solid MgSO4 and solid Na2CO3, filtered and concentrated to give the desired compound. MS (M+H)+ 185.

Provenance & Evidence