Sodium Hydroxide → 1-(2,5-Dibromophenyl)thiourea

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzoyl-3-(2,5-dibromo-phenyl)-thiourea II (3.90 g, 11.8 mmol) in THF (80 mL) was added NaOH solution (1.13 g in 20 mL H2O) at room temperature. The reaction mixture was then heated up to 60-65° C. overnight. After completion of the reaction (TLC monitoring) THF was distilled off followed by addition of water, and extracted with ethyl acetate (2×50 mL). The combined organic layers were combined and dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude residue was washed with mixture of hexane and diethyl ether (95:5) and dried under high vacuum to obtain the desired product as pale-yellow solid (2.5 g, 86%). 1H NMR (DMSO-d6, 400 MHz): δ 7.35 (dd, J=8.80 and 2.80 Hz, 1H), 7.48 (br s, 1H), 7.60 (d, J=8.40 Hz, 1H), 7.87 (d, J=2.40 Hz, 1H), 8.0 (br s, 1H) and 9.33 (br s, 1H). MS: 308.98 (M+H+).

Provenance & Evidence