Nitronium tetrafluoroborate → HCID 19101581, compound

HRID 1974480Notes

Reaction equation

F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].O.[ClH:10].[NH:11]1[CH:15]=[CH:14][N:13]=[C:12]1[C:16]1[CH:17]=[CH:18][C:19]2[C:20]([N:27]=1)=[N:21][C:22](=[O:26])[C:23](=[O:25])[N:24]=2>S1(CCCC1)(=O)=O.O.[OH-].[Na+]>[ClH:10].[NH:11]1[CH:15]=[CH:14][N:13]=[C:12]1[C:16]1[C:17]([N+:7]([O-:8])=[O:6])=[CH:18][C:19]2[C:20]([N:27]=1)=[N:21][C:22](=[O:26])[C:23](=[O:25])[N:24]=2

Participants

Conditions

Temperature: 120 °C

Procedure

In 10 ml of sulfolane was dissolved 1.01 g of -imidazolylpyrido[2,3-b]pyrazine-2,3-dione hydrochloride monohydrate followed by addition of 1.35 g of nitronium tetrafluoroborate, and the mixture was stirred at 120° C. for 4 hours. The reaction mixture was then allowed to cool to room temperature, diluted with 10 ml of water and neutralized with 1N aqueous sodium hydroxide solution. The resulting crystals were recovered by filtration and rinsed with a small amount of water. The resulting crystals were suspended in 2 ml of water followed by addition of a stoichiometric amount of 1N-hydrochloric acid and, further, 5 ml of ethanol. The crystals were recovered by filtration and dried under reduced pressure to provide 0.63 g of 6-imidazolyl-7-nitropyrido[2,3-b]pyrazine-2,3-dione hydrochloride.

Workup

temperatureto cool to room temperature
filtrationThe resulting crystals were recovered by filtration
washrinsed with a small amount of water
additionfollowed by addition of a stoichiometric amount of 1N-hydrochloric acid
filtrationThe crystals were recovered by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-53091135c9c84cf9b47f3d86854cae6b
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05283244

Reaction notes

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