Phosphorus pentachloride → HCID 12897713, compound

HRID 256819Notes

Reaction equation

[N+:1]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[C:9]([OH:11])=O)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)Cl>>[N+:1]([C:4]1[N:8]=[CH:7][N:6]2[C:5]=1[C:9](=[O:11])[N:6]1[CH:7]=[N:8][C:4]([N+:1]([O-:3])=[O:2])=[C:5]1[C:9]2=[O:11])([O-:3])=[O:2]

Participants

Reactant 2

HCID 24819Phosphorus pentachloride

HCID 862227941H-Imidazole-4-carboxylic acid, 5-nitro-

Product 1

HCID 12897713HCID 12897713, compoundYield 107.3%

Conditions

Temperature: 120 °C

Procedure

An intimate mixture of 5-nitroimidazole-4-carboxylic acid (2.0 g) and phosphorus pentachloride (2.67 g) was stirred and heated in an oil bath at 120° C. for 1 hour. The resulting yellow slurry was evaporated at 60° C./0.1 nun Hg for 30 minutes, to give 1,6-dinitro-5H,10H-diimidazo[1,5-a:1',5'-d]pyrazine-5,10-dione (1.90 g) in the form of a yellow solid, m.p. 249°-251° C. (with decomposition). [νmax (KBr disc) 1750 cm-1 ; m/e 278 (M+)].

Workup

customThe resulting yellow slurry was evaporated at 60° C./0.1 nun Hg for 30 minutes

Sources & evidence

ORD record: ord-e4cb59f2ef674804a40ecb6b6454c5d3
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05260291

Reaction notes

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