Oxalyl chloride → HCID 67266620, compound

Participants

Reaction Steps

4-(Chloromethyl)phenylacetic acid (5.0 g, 27.1 mmol) was suspended in dichloromethane (50 ml), and oxalyl chloride (9.2 ml, 0.11 mol) and N,N-dimethylformamide (2 drops) were added. After stirring at room temperature for 1 hr, and the mixture was concentrated under reduced pressure. Dichloromethane (50 ml) and tert-butyl carbazate (4.29 g, 32.5 mmol) were added to the residue, and the mixture was cooled to 0° C. N,N-diisopropylethylamine (14 ml, 81.3 mmol) was added dropwise, and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Diethyl ether was added to the residue and the resulting precipitate was collected by filtration. The filtrate was concentrated and added with diethyl ether to recover the secondary crystals. They were dried to give tert-butyl 2-{[4-(chloromethyl)phenyl]acetyl}hydrazinecarboxylate (5.9 g, primary and secondary crystals, total yield 73%) as a pale-yellow solid.

Provenance & Evidence