Water → HCID 70453742, compound

Participants

Reaction Steps

A mixture of 10.0 g of 1,3-diamino-7-diethylamino-8-methylphenoxazin-5-ium chloride (Brilliant Cresyl Blue, Eastman Kodak), 50.0 ml of acetic anhydride, 10.0 g of zinc dust and 10.0 ml of pyridine was maintained at 85° to 90° C. for approximately one hour. After cooling to room temperature, the reaction mixture was poured into a mixture of water and toluene and the resulting water layer was separated and discarded. The toluene solution was washed twice, first with water and then with saturated sodium chloride solution. The toluene was removed by evaporation at reduced pressure. The resulting residue was recrystallized from isopropanol and the solid obtained was recrystallized from ethanol to obtain 0.2 g of 1,9-dimethyl-4-acetamido-8-diethylaminoimidazophenoxazine (Formula I: R=R3 =CH3 ; R1 =R2 =C2H5), a white solid which melted at 217° to 218° C. A significant infrared maximum appeared at 1660 cm-1 (C=O;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure. Paper coated with an ink formulation of the product produced a purple-colored image when contacted with an applied voltage stylus.

Provenance & Evidence