Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoate → HCID 13589547, compound

HRID 2073624Notes

Reaction equation

HRID 2073624 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:12]([C:15](=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=O)[CH3:13]>C(O)C>[CH2:19]([O:18][C:16]([C:15]1[CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[N:6]2[CH:5]=[N:4][C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[NH:1][C:12]=1[CH3:13])=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 178470302HCID 178470302, compound

Product 1

HCID 13589547HCID 13589547, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2 g of 5-amino-4-ethoxycarbonylimidazole and 3.4 g of ethyl α-acetyl-3-nitrocinnamate in 50 ml of ethanol is refluxed under heating for 7 hours under a nitrogen atmosphere. The ethanol is removed under reduced pressure, the resulting oil is purified by column chromatography on silica gel with a mixture of chloroform and methanol as eluent. Recrystallization from a mixture of isopropyl alcohol and isopropyl ether gives 2.5 g of 3,8-diethoxycarbonyl-2-methyl-4-(3-nitrophenyl)-1,4-dihydroimidazo[1,5-a]pyrimidine, melting at 160°-162° C.

Workup

  1. temperatureunder heating for 7 hours under a nitrogen atmosphere
  2. customThe ethanol is removed under reduced pressure
  3. customthe resulting oil is purified by column chromatography on silica gel with a mixture of chloroform and methanol as eluent
  4. customRecrystallization
  5. additionfrom a mixture of isopropyl alcohol and isopropyl ether

Sources & evidence

ORD record
ord-63f6e462332445e089ef645c4824dbe3
Source dataset
uspto-grants-1990_04
Patent number
US04918074

Reaction notes

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