5-Chloro-2-methylphenyl isothiocyanate → 3-(5-Chloro-2-methyl-phenyl)-1-ethyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-thiourea

Participants

Reaction Steps

Prepared using Method A from 9.33 g (51 mmol) of 5-chloro-2-methyl-phenyl isothiocyanate and 4-ethylamino-1,3,5-trimethylpyrazole (7.2 g, 47 mmol) of step B to give 5.4 g of title compound as a white solid (70% yield, m.p. 144-145° C.). NMR (DMSO-d6, 400 MHz): 1.07 (t, 3H, CH2CH3), 2.04 (s, 3H, ArCH3), 2.07 (s, 3H, ArCH3), 2.11 (s, 3H, ArCH3), 3.82 (s, 3H, NCH3), 4.23 (m, 2H, CH2CH3), 7.02 (s, 1H, ArH), 7.19 ( s, 2H, ArH), 8.41 (s, 1H, NH). MS [EI, m/z]: 336 [M]+, 195 [b.p.] Anal. Calc'd. for C16H21ClN4S: C, 57.04; H, 6.28; N, 16.63 Found: C, 56.93; H, 6.18; N, 16.44

Provenance & Evidence