4-Nitrobenzyl bromide → Pseudourea, 2-(p-nitrobenzyl)-2-thio-, monohydrobromide

Participants

Reaction Steps

To a solution of thiourea (3.87 g, 50.92 mmol) in acetone (15 mL) was added a solution of 1-(bromomethyl)-4-nitrobenzene (10 g, 46.29 mmol) in acetone (15 mL) and the mixture stirred at rt for 2 h upon which a white precipitate formed. After completion of reaction (by TLC), the mixture was filtered and solid washed with EtOAc and acetone respectively to afford the desired product as off-white solid (12.0 g, 89%). 1H NMR (DMSO-d6): δ 9.17 (br s, 4H), 8.24 (d, J=8.40 Hz, 2H), 7.70 (d, J=8.40 Hz, 2H) and 4.66 (s, 2H). MS: 212.08 [M+H]+

Provenance & Evidence