Triazine Preparation - 1-(m-nitrophenyl)-3,3-dimethyltriazene
The following preparation is a good example of the standard laboratory procedure for converting a diazonium salt into a triazine. The reaction involves the simple nucleophilic attack of dimethyl amine at the remote nitrogen of the aryl diazonium salt. The reaction is performed in the presence of sodium carbonate which acts as a base to neutralize the hydrochloric acid generated.
Pulverized sodium carbonate monohydrate (435 g, 3.5 mol) is added in portions with rapid stirring to 1.25 liters of water. Crushed ice is added to the resulting suspension until the temperature has been lowered to 10 °C followed by the addition of a 25% solution of dimethyl amine (212 g, 1.18 mol). To the reaction mixture is then added with rapid stirring an ice cold solution of m-nitrobenzenediazonium chloride beneath the surface of the reaction mixture over a period of approximately 30 minutes. Ice is added throughout the addition in order to maintain the temperature at approximately 10 °C. The resulting mixture is then stirred for an additional 20 minutes.
The crude product is collected via filtration and the filter cake is washed with water with mixing (2X1.25 liters). The filter cake is then pressed to remove moisture and dissolved in 1 liter of boiling 95% ethanol. The resulting solution is cooled in a water bath and the resulting crystalline product is collected and washed with 95% ethanol (2X100 mL) to afford the title compound.