HCID 11221833, compound → Quinacridone

Participants

Reaction Conditions

Reaction Steps

To 320 g of polyphosphoric acid (116.5% phosphoric acid) was sequentially added 6.8 g of 2,5-bis[4-(3-methoxypropylsulfamoyl)anilino]-1,4-cyclohexadiene-1,4-dicarboxylic acid, dimethyl ester and 64 g of 2,5-dianilino-3,6-dihydroterephthalic acid over a period of 45 minutes, the temperature being maintained below 110° C. The reaction mixture was stirred at 100° to 110° C. for one hour and then allowed to cool to 85° C., after which the phosphoric acid concentration was reduced to 85% by the slow addition of chilled water. The mixture was stirred at 85° to 90° C. for 30 minutes, then slowly poured into 1200 ml of ice/water and stirred at less than 30° C. for an additional hour. The solid component was collected by filtration and washed with water. The resultant wet presscake was reslurried in 181.3 g of methanol and 73.9 g of water and stirred until uniform. After 37.3 g of 50% aqueous sodium hydroxide was added, the slurry was stirred at less than 35° C. for one hour. The slurry was then heated to 60° C., diluted with 12.6 g of water, and heated at reflux for 30 minutes. After the slurry was allowed to cool to 60° C., 37.3 g of 92% sodium 3-nitrobenzenesulfonate and 31.6 g of water were added sequentially. After ten minutes, the slurry was heated at 88° C. for 15 hours. Upon being cooled to room temperature, the solid component was isolated by filtration and washed with water. The wet presscake cake was reslurried in 357.1 g of methanol and 357.1 g of water (which includes the amount of water in the presscake). When the slurry became uniform, 95.2 g of 50% aqueous sodium hydroxide and an additional 60.0 g of 92% sodium 3-nitrobenzenesulfonate were added. The resultant slurry was heated in a sealed system at 115° to 120° C. for six hours. Upon being cooled to room temperature, the solid component was isolated by filtration and washed with water. The wet presscake cake was dried to give 41.0 g of gamma quinacridone.

Provenance & Evidence