Toluene → Carbanilide

Participants

Reaction Steps

The above reaction was carried out in a high-grade stainless steel autoclave fitted with a polytetrafluoroethylene beaker of 100 cm3 capacity. 0.0373 g (0.1 mmole) of N,N′-bis(salicylidene)-1,2-phenylenediaminocobalt(II), 0.0172 g (0.1 mmole( of p-toluenesulfonic acid, 4.6498 g (50.0 mmole) aniline, 1.2318 g (10.0 mmole) of nitrobenzene and 8.69 g (10 mmole) of toluene were mixed in the autoclave. The autoclave was flushed three times with gaseous nitrogen and then was pressurized with 50 bar carbon monoxide. After the gas supply was interrupted, the autoclave was inserted into an aluminum block that had been preheated to 200° C. Following 5 minutes, the autoclave reaction temperature reached 170° C. which thereupon was kept constant. Following 6 h of reaction, the autoclave was cooled with cold water and ice and reached room temperature in 5 minutes. The reaction mixture was filtered off and the solid substance so obtained was washed with toluene (3×10 ml). Thereupon the solid substance was dried in high vacuum for 4 h. Characterization was implemented by 1H-NMR, MS, CHN analysis and melting point. This test, not yet optimized, gave 3.0414 g of N,N′-diphenylurea, relating to a yield of 23.9%.

Provenance & Evidence