Urea → HCID 178493796, compound

HRID 628994Notes

Reaction equation

HRID 628994 reaction equation
[O:1]([CH2:3][C:4]([O:6][CH3:7])=O)C.[CH:8](OCC)=O.C[O-].[Na+].[NH2:16][C:17]([NH2:19])=[O:18]>C1(C)C=CC=CC=1.CCO>[CH3:7][O:6][C:4]1[C:3]([OH:1])=[N:16][C:17]([OH:18])=[N:19][CH:8]=1

Participants

7

Reactant 4

HCID 1176UreaHCID 8025Ethyl formateHCID 80507Methyl methoxyacetateHCID 10942334Sodium Methoxide2×

Product 1

HCID 178493796HCID 178493796, compoundYield 23.88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of methyl methoxylacetate (15 ml, 1.0 eq) and ethyl formate (12.18 ml, 1.0 eq) was added dropwise to slurry of sodium methoxide (8.17 g, 1.0 eq) in toluene (100 ml) at 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 NaOMe (4.10 g, 0.5 eq) in EtOH (100 ml) was refluxed at 110° C. for 4 hrs. After the solvent was dried in vacuo, water and conc. HCl solution (5<pH<4) were added. After formation of white precipitate, the mixture was filtered and dried solid in vacuo. A product was obtained as a white solid (5.14 g, 23.88%)

Workup

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

Sources & evidence

ORD record
ord-36064b518e004d40af80b450da8d856a
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

Loading…