5-(1H-Tetrazol-1-yl)isophthalic acid synthesis

Yield:207730-78-7 82%

Reaction Conditions:

with sodium azide;acetic acid at 80 - 90; for 6 h;

Steps:

1; 2.1 1. Synthesis of S-(lH-fetrazoI-I-yl)-l,3-beiizeiiedicarbosy e add

1. Synthesis of S-(lH-fetrazoI-I-yl)-l,3-beiizeiiedicarbosy e add Glacial acetic acid (10.0 ml) was added with stirring to a suspension of 5- aminoisophthalic acid (4.54 g, 0.025 mol), and sodium azide (1.79 g, 0.0275 mol) in triethyl orthoformate (14.2 mL, 0.075 mol), and the mixture was stirred at 80-90 °C for 6 h. The reaction mixture was cooled, and concentrated hydrochloric acid (4.2 mL, 0.05 mol) and water (12.5 mL) were added. The precipitated solid was separated by filtration, washed with water, and dried. The obtained raw product was recrystallized from DMF. Yield: 82 % (4.79 g). NMR (500 MHz, DMSO-ifc, ppm): δ 13.78 (s, 2H, -CO2H), 10.33 (s, 1H, -N₄CH), 8.65 (s, 2H, -CeH₃), 8.55 (s, 1H, -CeH₃).

References:

WO2016/154300,2016,A1 Location in patent:Page/Page column 12; 17