Nitric Acid → 6-Nitrothieno(2,3-b)pyrazine-2,3(1H,4H)-dione

HRID 1974994Notes

Reaction equation

HRID 1974994 reaction equation
[NH:1]1[C:6](=[O:7])[C:5](=[O:8])[NH:4][C:3]2[S:9][CH:10]=[CH:11][C:2]1=2.[N+:12]([O-])([OH:14])=[O:13]>C(OC(=O)C)(=O)C>[N+:12]([C:10]1[S:9][C:3]2[NH:4][C:5](=[O:8])[C:6](=[O:7])[NH:1][C:2]=2[CH:11]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 19100709Thieno[2,3-b]pyrazine-2,3(1H,4H)-dione

Product 1

HCID 191007966-Nitrothieno(2,3-b)pyrazine-2,3(1H,4H)-dioneYield 26%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Thieno[2,3-b]pyrazine-2,3(1H,4H)-dione (1.00 g, 5.95 mmol) was reacted with fuming nitric acid (0.374 ml, 8.9 mmol) in acetic anhydride following the procedure outlined in example 4 (Method F). The crude product (655 mg) was recrystallized from acetic acid to afford 325 mg (26%) of the title compound. M.p.>300° C. 1H-NMR (DMSO-d6, δ): 7.58 (s, 1H), 12.1 (s, 1H), 12.62 (s, 1H).

Workup

  1. customThe crude product (655 mg) was recrystallized from acetic acid

Sources & evidence

ORD record
ord-24ffe20e6b9e4b9cb84c22d38a6a91ba
Source dataset
uspto-grants-1994_02
Patent number
US05284847

Reaction notes

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