1H-Imidazole-4,5-dicarbonyldichloride(9CI) synthesis

Yield:-

Reaction Conditions:

with thionyl chloride in N,N-dimethyl-formamide;toluene at 90; for 16 h;

Steps:

1 6.5.1 Diphenyl 5,10-dioxo-5,10-dihydrodiimidazo[1,5-a:1′,5′-d]pyrazine-1,6-dicarboxylate (17)

To a solution of imidazole-4,5-dicarboxylic acid (400 mg, 2.56 mmol) in 5 mL of toluene was added 1.12 mL of thionyl chloride (15.38 mmol) and 0.1 mL of DMF at rt. The reaction mixture was stirred at 90 °C for 16 h. Then 5 mL of DCM was added to the suspension and the solvent was removed by evaporation. This process was repeated twice. The resulting acid chloride was dissolved in 10 mL of DCM and cooled to 0 °C. Phenol (2.82 mmol) in 5 mL of DCM was added and the resulting solution was stirred at 0 °C for 1 h. Then the solid product was collected by vacuum filtration, washed with 10 mL of DCM twice, and dried under vacuum to yield 0.632 g of crude product 17 (83.6 % over two steps) as a tan solid. ¹H NMR (300Hz, DMSO) δ 9.12 (s, 2H), 7.52-7.56 (m, 4H), 7.34-7.40 (m, 6H); ESI-MS: 429 [M+1]⁺

References:

Serrao, Erik;Xu, Zhong-Liang;Debnath, Bikash;Christ, Frauke;Debyser, Zeger;Long, Ya-Qiu;Neamati, Nouri [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 19,p. 5963 - 5972]