p-Toluenesulfonic acid → HCID 78165277, compound

Reaction equation

[C:1]([C:9]1[CH:14]=[C:13]([C:15](=O)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[C:11]([C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:31][NH:32][C:33]([NH2:35])=[S:34].C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C:1]([C:9]1[CH:14]=[C:13]([C:15](=[N:31][NH:32][C:33]([NH2:35])=[S:34])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[C:11]([C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Procedure

To a round bottom flask containing methanol (16 mL) was added 1,3,5-tribenzoylbenzene (0.250 g, 0.640 mmol). This was stirred under nitrogen and heated to reflux. Thiosemicarbazide (0.05536 g, 0.608 mmol) was then added to the flask, followed by p-toluenesulfonic acid (0.00122 g, 0.0064 mmol). The reaction mixture was stirred at reflux for 14 h. The crude mixture was purified using column chromatography, eluting with 35% ethyl acetate in hexanes, however the product still contained impurities and was submitted for testing without further purification. HRMS (ESI) calculated for C28H21O2N3SH+ (M+H)+ 464.14272, found 464.14267. Compound 25 was estimated to be approximately 80% pure by NMR, and was submitted for biological testing without further purification.