Benzaldehyde → HCID 86605710, compound

HRID 2221549Notes

Reaction equation

HRID 2221549 reaction equation
Cl.[NH:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].C(=O)([O-])O.[Na+].[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[CH:26]=[C:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])C>O.C(O)C>[CH:15](=[N:3][N:2]([CH:26]=[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6871Diethyl (ethoxymethylene)malonateHCID 516892Sodium BicarbonateHCID 11593468Acetic acid, 2-hydrazinyl-, ethyl ester, hydrochloride (1:1)

Product 1

HCID 86605710HCID 86605710, compoundYield 23.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of ethyl hydrazinoacetate hydrochloride (15.5 g), sodium hydrogen carbonate (8.40 g), water (15 mL) and ethanol (100 mL) was stirred at room temperature for 30 min. Benzaldehyde (10.61 g) was added to the reaction mixture, and after stirring for 1 hr, diethyl ethoxymethylenemalonate (21.6 g) was added. The mixture was heated under reflux for 15 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give diethyl [(2-benzylidene-1-(ethoxycarbonylmethyl)hydrazino]methylene}malonate as colorless crystals (8.75 g, yield 23%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 105-106° C.

Workup

  1. stirringafter stirring for 1 hr
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 15 hrs
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-2528159cd5f94c8b9432e7080f1a5423
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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