Formamidine acetate → HCID 178470709, compound

HRID 1458665Notes

Reaction equation

HRID 1458665 reaction equation
C([CH:4]([CH2:10][C:11]([O-:13])=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)C.[C:14](O)(=O)[CH3:15].[CH:18]([NH2:20])=[NH:19].C[O-].[Na+]>C(O)C>[OH:13][C:11]1[C:10]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:14]([CH3:15])[N:20]=[CH:18][N:19]=1

Participants

5

Reactant 3

HCID 160693Formamidine acetateHCID 10942334Sodium MethoxideHCID 22097404HCID 22097404, compound

Product 1

HCID 178470709HCID 178470709, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

216.24 g (1.0 mol) of ethyl acetylsuccinate and 104.11 g (1.0 mol) of formamidine acetate were placed in 500 ml of ethanol, and 360.13 g (2.0 mol) of 30% methanolic sodium methylate solution were added dropwise at 0° C. The mixture was stirred at room temperature for 6 hours and concentrated and the residue was taken up in toluene/water. The aqueous phase was brought to a pH of 3-4 with conc. hydrochloric acid and extracted by stirring a number of times with dichloromethane. Drying and concentration of the combined dichloromethane phases left a resinous solid. This solid was stirred with a mixture of diisopropyl ether and ethyl acetate (2:1) which was then filtered with suction to leave 55.6 g (28.3% of theory) of colorless crystals of m.p. 148° to 149° C.

Workup

  1. concentrationconcentrated
  2. extractionextracted
  3. stirringby stirring a number of times with dichloromethane
  4. customDrying
  5. waitconcentration of the combined dichloromethane phases left a resinous solid
  6. stirringThis solid was stirred with a mixture of diisopropyl ether and ethyl acetate (2:1) which
  7. filtrationwas then filtered with suction
  8. customto leave 55.6 g (28.3% of theory) of colorless crystals of m.p. 148° to 149° C.

Sources & evidence

ORD record
ord-db8d8ad859a34b5f8b3dca8df5a647c7
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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