Dimethylformamide → HCID 86619756, compound

Participants

Reaction Conditions

Reaction Steps

To a 50 mL recovery flask was added 4-chloro-3-trifluoromethylphenyl isocyanate (759 mg, 3.80 mmol, 1.0 eq.) and CH3CN (8 mL). The solution was cooled to 0° C. In a separate flask was prepared a solution of N-bromophenyl-N-methylhydrazine 41 (759 mg, 3.80 mmol, 1.0 eq.) and Et3N (529 μL, 3.80 mmol, 1.0 eq.) in CH3CN (4 mL). DMF (2 mL) was added to the solution to aid in solubility of the hydrazine adduct. The solution was added to the reaction flask dropwise via syringe. After stirring for 1 h, LC/MS indicated the completion of the reaction. The reaction was concentrated and then diluted with EtOAc (100 mL). The organic phase was washed with water (50 mL) and brine (30 mL). The combined aqueous layers were extracted with EtOAc (30 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give a yellowish oil which later crystallized (251 mg, 16%). The crude material was used without further purification.

Provenance & Evidence