Acetylacetone → HCID 15725413, compound

Participants

Reaction Steps

A slurry of 0.5 g (2.2 mmole) of 3-amino-5-benzylthio-4-cyanopyrazole in 15 ml glacial HOAc was stirred at room temperature as 0.44 g (4.4 mmole) of 2,4-pentanedione was added. The mixture was stirred at room temperature for 3 hours. The white solid was collected by filtration, washed with HOAc, and dried to give 0.62 g (95.4 percent) of product as a white powder, m.p. 140° C. The analytical sample was recrystallized from 2-propanol. 1H NMR (DMSO-d-6): 7.5 (m, 2H, benzene), 7.3 (m, 3H, benzene), 7.1 (s, 1H, pyrazolopyrimidinyl H-6), 4.5 (s, 2H, CH ), 2.7 (s, 3H, CH ), 2.5 (s obscured by DMSO, 3H, CH3). 13C NMR (DMSO-d-6): 163.3, 155.3, 150.5, 146.7, 137.0, 129.1, 128.3, 127.3 112.8, 111.1, 79.0, 34.5, 24.1, 16.3. IR (KBr): 2220, 1615, 1550 cm-1. Analysis: Calculated for C16H14N4S: C, 65.28; H, 4.79; N, 19.03; S, 10.89. Found: C, 65.11; H, 4.64; N, 18.95; S, 11.03.

Provenance & Evidence