Sodium Hydroxide → HCID 178514156, compound

Participants

Reaction Steps

To a solution of 5-amino-3-(2-bromophenyl)pyrazole (1.3 g, 5.46 mmol) in THF (20 mL) was added dropwise benzoyl isothiocyanate (0.81 mL, 6.0 mmol). The reaction mixture was stirred at room temperature for 3 hours, then 4 N aqueous solution of NaOH (4 mL) was added, and the reaction mixture was further stirred at 50° C. for 2 hours. The reaction mixture was cooled to room temperature, neutralized to pH 7 with a saturated solution of NH4Cl, and extracted with EtOAc (3×). The combined organic layers were directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide 1.62 g (quant.) of [5-(2-bromo-phenyl)-2H-pyrazol-3-yl]-thiourea as a yellowish foam. 1H-NMR (d6-DMSO) δ: 12.8 (broad s, 1H), 10.4 (broad s, 1H), 8.99 (broad s, 1H), 8.52 (broad s, 1H), 7.76 (d, 1H), 7.50 (m, 2H), 7.36 (t, 1H), 6.24 (broad s, 1H).

Provenance & Evidence