N,N-Dimethylaniline → HCID 13562765, compound

Participants

Reaction Steps

The product obtained in Step 1 (12 g) was suspended in 100 ml of phosphorus oxychloride, 5.9 g of N,N-dimethylaniline was added dropwise to this suspension at 0° C. with stirring over a period of ten minutes, and the mixture was stirred at room temperature for 30 minutes and then refluxed for four hours. Removing excess phosphorus oxychloride by distillation under normal pressure gave about 50 ml of a reddish brown oil. It was dissolved in 300 ml of dichloromethane, the solution was washed with 500 ml of saturated sodium bicarbonate solution, then with 80 ml of saturated sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The dried reddish yellow filtrate was concentrated to about 30 ml, and crystallized from 20 ml of n-hexane, affording 8.5 g of the objective compound as faint yellow crystals.

Provenance & Evidence