3-Nitrobenzaldehyde → HCID 682109, compound

HRID 1940502Notes

Reaction equation

HRID 1940502 reaction equation
C([N:4]1[CH2:9][C:8](=[O:10])[N:7]([C:11](=[O:13])[CH3:12])[CH2:6][C:5]1=[O:14])(=O)C.[N+:15]([C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[CH:21]=O)([O-:17])=[O:16].C(N(CC)CC)C>CN(C=O)C>[C:11]([N:7]1[CH2:6][C:5](=[O:14])[NH:4][C:9](=[CH:21][C:20]2[CH:23]=[CH:24][CH:25]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=2)[C:8]1=[O:10])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 8471TriethylamineHCID 5403711,4-Diacetyl-2,5-piperazinedione

Product 1

HCID 682109HCID 682109, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Diacetyl-2,5-piperazinedione (1 equivalent), prepared by the published procedure mentioned in Example 3, was treated with 3-nitrobenzaldehyde (1 equivalent) in the presence of triethylamine (1 equivalent) in DMF at room temperature for 18-20 hrs. The title compound was obtained in 9% yield together with 1-acetyl-3-(3-nitrobenzylidene)-2,5-piperazinedione (66% yield). Characterising data are set out in Example 16.

Sources & evidence

ORD record
ord-2607fe53016f47c89e654e8976152997
Source dataset
uspto-grants-1997_12
Patent number
US05700804

Reaction notes

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