2,6-Dichlorobenzaldehyde → (3Z)-1-acetyl-3-(2,6-dichlorobenzylidene)-2,5-piperazinedione

HRID 442654Notes

Reaction equation

HRID 442654 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.[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:17]=1[CH:18]=O.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:18]\[C:17]2[C:16]([Cl:15])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:24])/[C:8]1=[O:10])(=[O:13])[CH3:12]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 8471TriethylamineHCID 5403711,4-Diacetyl-2,5-piperazinedione

Product 1

HCID 21308865(3Z)-1-acetyl-3-(2,6-dichlorobenzylidene)-2,5-piperazinedioneYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,4-Diacetyl-2,5-piperazinedione prepared by the published procedure mentioned in Reference Example 3, was stirred in DMF with 2,6-dichlorobenzaldehyde and triethylamine and heated to 120°-130° C. for 1-3 h. The title compound was obtained with a yield of 40%.

Workup

  1. temperatureheated to 120°-130° C. for 1-3 h

Sources & evidence

ORD record
ord-580416b22eb44c648a525512ce786adc
Source dataset
uspto-grants-1999_04
Patent number
US05891877

Reaction notes

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