Formamidine acetate → HCID 18945467, compound

HRID 399841Notes

Reaction equation

HRID 399841 reaction equation
[CH3:1][N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=1)[C:10]([O:12][CH3:13])=[O:11])=O.CC(O)=O.C(N)=[NH:23].C[O-].[Na+]>CO>[N:2]1[CH:3]=[CH:4][C:5]([C:7]2[CH:8]=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])=[N:23][CH:1]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 54100790HCID 54100790, compound

Product 1

HCID 18945467HCID 18945467, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of methyl 3-(3-dimethylaminopropenoyl)benzoate (1.4 g), formamidine-acetate (2.8 g) and 28% methanolic sodium methoxide (5.2 ml) in methanol (38 ml) was heated under reflux for 64 hours under stirring. The solvent was removed by concentration and to the residue was added water. The mixture was adjusted to pH 9 with 20% aqueous potassium carbonate solution and the mixture was extracted with ethyl acetate. The extract layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with the solution of diisopropyl ether and n-hexane and the precipitate was collected by filtration to give methyl 3-(pyrimidin-4-yl)benzoate (0.8 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 64 hours
  3. customThe solvent was removed by concentration and to the residue
  4. additionwas added water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was triturated with the solution of diisopropyl ether and n-hexane
  10. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-e8eae9010d4c402d9f9cd7f3462939c9
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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