Triethylamine → HCID 90411149, compound

Participants

Reaction Steps

To a solution of tert-butyl 1-(thiophen-2-yl)hydrazinecarboxylate (100 mg, 0.467 mmol) in THF (5 mL) was added triethylamine (64 μL, 0.476 mmol, 1 eq.) and 4-chlorobenzoyl chloride (60 μL, 82 mg, 0.467 mmol, 1 eq.), and the resulting mixture was stirred for 1 hour at room temperature. A sample of the reaction mixture (quenched in water, and extracted with EtOAc) showed the presence of the intermediate crude product tert-butyl 2-(4-chlorobenzoyl)-1-(thiophen-2-yl)-hydrazinecarboxylate, as determined by NMR. The reaction mixture was then poured in water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The crude product (278 mg) was purified by automated column chromatography (EtOAc/heptane) to yield tert-butyl 2-(4-chlorobenzoyl)-1-(thiophen-2-yl)-hydrazinecarboxylate (127 mg, 360 mmol, yield 77%) as a light brown solid with an HPLC purity of greater than 99%. LC-MS (M−1) 351 (C16H17ClN2O3S-1, expected 352.06).

Provenance & Evidence