Hydrazine hydrate (1:1) → HCID 135616744, compound

HRID 1277627Notes

Reaction equation

HRID 1277627 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].O.[NH2:7]N.[C:9]([NH:14][CH:15]([CH3:23])[C:16](=O)[C:17](OCC)=[O:18])(=[O:13])[CH2:10][CH2:11][CH3:12]>C(O)C>[C:9]([NH:14][CH:15]([C:16]1[C:17](=[O:18])[NH:4][C:2]([CH3:3])=[N:5][N:7]=1)[CH3:23])(=[O:13])[CH2:10][CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67170Acetamidine monohydrochlorideHCID 11736048HCID 11736048, compound

Product 1

HCID 135616744HCID 135616744, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To an ice-cold solution of acetamidine hydrochloride (66.2 g) in absolute ethanol (600 ml) was slowly added a solution of hydrazine hydrate (35 g) in absolute ethanol (20 ml) over 20 minutes. After completion of the addition stirring was continued at room temperature for 10 minutes. A solution of ethyl 3-butyramido-2-oxo-butyrate (151 g) in absolute ethanol (100 ml) was then added and the mixture heated at 65°-70° with stirring for 20 hours. The precipitated ammonium chloride was removed by filtration and the filtrate concentrated in vacuo whereupon the triazinone separated. Ethyl acetate (ca. 300 ml) was added to aid the precipitation and the solid was collected. The filtrate was concentrated to give a second crop which was combined with the first and recrystallised from ethanol, 28.6 g. A further recrystallisation from ethanol afforded an analytical sample, m.p. 235°-237°.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture heated at 65°-70°
  3. stirringwith stirring for 20 hours
  4. customThe precipitated ammonium chloride was removed by filtration
  5. concentrationthe filtrate concentrated in vacuo whereupon the triazinone
  6. customseparated
  7. additionEthyl acetate (ca. 300 ml) was added
  8. customthe precipitation
  9. customthe solid was collected
  10. concentrationThe filtrate was concentrated
  11. customto give a second crop which
  12. customrecrystallised from ethanol, 28.6 g
  13. customA further recrystallisation from ethanol
  14. customafforded an analytical sample, m.p. 235°-237°

Sources & evidence

ORD record
ord-38c6b8f5d2394674b1cf46e9322b9f6b
Source dataset
uspto-grants-1981_07
Patent number
US04278673

Reaction notes

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