3-Nitroaniline → (3-Nitrophenyl)thiourea

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C. ) and stirred solution of 1-amino-3-nitrobenzene (10 g) in anhydrous tetrahydrofuran (500 ml), under nitrogen, was added thiophosgene (5.6 ml) dropwise. After 5 min triethylamine (29 ml) was added dropwise and the mixture stirred for a further 5 min at 0° C. then at room temperature for 10 min. The mixture was then re-cooled to 0° C. and ammonia gas bubbled through the mixture for 15 min. The resultant solid was removed by filtration and the filtrate evaporated in vacuo to afford a gum which was triturated with ethyl acetate to give the thiourea (7.3 g) as a solid. 1H NMR (250 MHz, D6 -DMSO)δ7.59 (1H, dd, J=8.2 and 8.2 Hz), 7.83 (1H, m), 7.92 (1H, m), 8.64 (1H, m), 10.09 (1H, brs). MS (CI, NH3) 197 (M+).

Provenance & Evidence