Sodium Acetate → HCID 86602956, compound

Participants

Reaction Conditions

Reaction Steps

Sodium 3-{(2Z)-5-{[(Carboxymethoxy)acetyl]methylamino}-2-[(2E,4Z)-4-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)but-2-enylidene]-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl}propane-1-sulfonate (24) and Sodium 3-{(2Z)-6-{[(Carboxymethoxy)acetyl]-methylamino}-2-[(2E,4Z)-4-(1,1-dioxido-3-oxo-1-benzothien-2(3H)-ylidene)but-2-enylidene]-1,3-benzothiazol-3(2H)-yl}propane-1-sulfonate (25). A mixture of the quaternary salt (22 or 23, 0.5 mmol) and enol ether 9 (0.625 g, 2.50 mmol) in 20 mL of a chloroformacetic acid mixture (1:1) was magnetically stirred at 60° C. under nitrogen. A solution of 0.200 g of sodium acetate in 5 mL of acetic acid was added by drops to the reaction mixture. The stirring was continued for an additional 24 h. After cooling the dye 25 crystallized from the reaction mixture and was separated by filtration and purified by recrystallization from acetic acid. The reaction mixture containing dye 24 was evaporated in a vacuum, and the pure dye was isolated by chromatography over silica gel, eluting with acetone-acetic acid (5:1), followed by recrystallization from acetic acid.

Provenance & Evidence