4-Nitroaniline → HCID 57169013, compound

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Reaction Steps

In Example 106, reaction of compound 340 with aminomethylbenzene 341 yielded the model compound 342 containing a thiourea linkage, as follows: To a solution of isothiocyanate 340 (1.80 g, 10 mol, prepared in Example 105 from the p-nitro aniline 339), benzylamine 341 (1.64 mL, 15 mmol) was added dropwise. The resulting mixture was stirred for 16 hours, then evaporated. The solid residue was washed on a filter sequentially with 2N HCl (5×10 mL), and H2O (5×5 mL), then dried in vacuo to produce a crude product that was crystallized from EtOAc to yield 2.190 g (76% yield) of benzyl-(4-nitrophenyl) thiourea 342 as an orange powder. Relevant data: mp 151°-152° C. (from EtOAc); 1H NMR (DMSO-d6): δ4.74 (s, 2H), 7.34 (m, 5H), 7.84 (d, 2H, J=9 Hz), 8.15 (d, 2H, J=9 Hz), 8.65 (s, 1H, NH), 10.21 (s, 1H, NH); 13C NMR (DMSO-d6): δ48.17, 121.62, 125.34, 128.04, 128.55, 129.30, 139.11, 142.92, 147.28, 181.36; MS m/e (1%): 287 (M+, 22), 180 (100), 150 (51), 138 (21), 122 (43), 106 (81), 107 (56), 91 (95).

Provenance & Evidence