Urea → HCID 178467208, compound

HRID 629005Notes

Reaction equation

HRID 629005 reaction equation
[O:1]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=O)CC.[CH:10](OCC)=O.[O-]CC.[Na+].[NH2:19][C:20]([NH2:22])=[O:21]>C1(C)C=CC=CC=1.CCO>[CH2:8]([O:7][C:5]1[C:4]([OH:1])=[N:19][C:20]([OH:21])=[N:22][CH:10]=1)[CH3:9]

Participants

7

Reactant 4

HCID 1176UreaHCID 8025Ethyl formateHCID 69955Ethyl ethoxyacetateHCID 2723922Sodium ethoxide2×

Product 1

HCID 178467208HCID 178467208, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl ethoxylacetate (20 g, 1.0 eq) and ethyl formate (11.21 ml, 1.0 eq) was added dropwise to a slurry of sodium ethoxide (10.3 g, 1.0 eq) in toluene (100 ml) in ice both. After dropping at room temperature and stirring overnight, the resulting solution was dried in vacuo. Then a mixture of residue, urea (9.09 g, 1.0 eq) and sodium ethoxide (10.3 g, 1.0 eq) in EtOH (100 ml) was refluxed at 110° C. for 6 hrs. After the solvent was dried in vacuo, water and conc. HCl solution (5<pH<4) were added. After formation of white precipitates, the mixture was filtered and dried solid in vacuo. A product was obtained as a white solid (7.76 g, 32%)

Workup

  1. customAfter dropping at room temperature
  2. customthe resulting solution was dried in vacuo
  3. dry with materialAfter the solvent was dried in vacuo, water and conc. HCl solution (5<pH<4)
  4. additionwere added
  5. filtrationAfter formation of white precipitates, the mixture was filtered
  6. customdried solid in vacuo

Sources & evidence

ORD record
ord-f5c535d10fd34c5ab42fd0cfb130d5fb
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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