Working Up Reaction

Today I had run one reaction: nitrosation of diphenylamine. TlC shows the reaction works pretty well and no starting materials exists. Because the product is one precipitate. So I try to get the product by filtration. Because there is still product in the RBF after the dumping, I try to wash the reaction RBF using the filtrate to get a high yield. However I forget at this time the temperature of the filtrate is higher that the reaction temperature of 5 degree. Because of this, some of the product was converted to the starting materials.

 

lesson: if the reaction include highly active reagent such as carbon anion and nitrous acid, first quenching the reaction then conducting other manipulation.