Aniline → HCID 19890958, compound

Participants

Reaction Steps

To a solution of 7 g (0.024 mol) 2-(2-picolylseleno)benzoic acid (from Example 1) and 2.4 g (0.024 mol) triethylamine in 40 ml dichloromethane which has been cooled to 0°-5° C. is added 6 g (0.024 mol) bis(2-oxo-3-oxazolidinyl)phosphoryl chloride in solid form as one portion. After stirring for 20 minutes a solution of 2.2 g (0.024 mol) aniline in 5 ml dichloromethane and a solution of 2.4 g (0.024 mol) triethylamine in 5 ml dichloromethane and a solution of 2.4 g (0.024 mol) triethylamine in 5 ml dichloromethane are added dropwise within 5 min, after 16 h at room temperature the reaction mixture is washed with 100 ml water. The organic phase is extracted successively with 100 ml 10% NaHCO3 solution, 100 ml 10% citric acid and 100 ml water. The organic phase is dried over sodium sulfate and the solvent removed under water pump vacuum. The solid crude product (6.3 g) is recrystallized from 35 ml 2-propanol.

Provenance & Evidence