Urea → HCID 178492489, compound

HRID 1179672Notes

Reaction equation

HRID 1179672 reaction equation
[O-]CC.[Na+].[Na].CN(C)[CH:8]=[C:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH:10]=O.[NH2:22][C:23]([NH2:25])=[O:24]>C(O)C.C(O)(=O)C.O>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[N:22][C:23]([OH:24])=[N:25][CH:10]=2)=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 1176UreaHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 544980242-(p-Methoxyphenoxy)-3-(dimethylamino)acrolein

Product 1

HCID 178492489HCID 178492489, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium ethoxide, prepared from sodium (0.80 g, 35.0 mmol), 3-dimethylamino-2-(4-methoxy-phenoxy)-propenal (3.87 g, 17.5 mmol) and urea (2.10 g, 35.0 mmol) in ethanol (25 ml) was heated at reflux for 4 hours. Water (1 ml) was added and heating was continued for an additional 2 hours. The solution was cooled to room temperature and neutralised with glacial acetic acid. Most of the solvent was removed by evaporation in vacuo. Water was added and the precipitate was isolated by suction, followed by drying in a vacuum oven, yielding the title compound (0.80 g, 21% yield) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureheating
  4. customMost of the solvent was removed by evaporation in vacuo
  5. additionWater was added
  6. customthe precipitate was isolated by suction
  7. customby drying in a vacuum oven

Sources & evidence

ORD record
ord-27620a4fc0da47718656a7f3290bcad7
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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