Hydrazine hydrate (1:1) → HCID 135616752, compound

HRID 1277624Notes

Reaction equation

HRID 1277624 reaction equation
O.[NH2:2]N.Cl.[C:5]([NH2:8])(=[NH:7])[CH3:6].C([O:11][C:12](=O)[C:13](=O)[CH:14]([NH:16][C:17](=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20])[CH3:15])C>C(O)C>[C:17]([NH:16][CH:14]([C:13]1[C:12](=[O:11])[NH:7][C:5]([CH3:6])=[N:8][N:2]=1)[CH3:15])(=[O:22])[CH2:18][CH:19]([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67170Acetamidine monohydrochlorideHCID 12621985HCID 12621985, compound

Product 1

HCID 135616752HCID 135616752, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Hydrazine hydrate (100%, 78 ml, 80 g) in absolute ethanol (40 ml) was added with stirring over a period of 15 minutes to a solution of acetamidine hydrochloride (151 g) in absolute ethanol (1200 ml) cooled to 5°. The mixture was stirred for a further 10 minutes, then ethyl-3-isovaleramido-2-oxobutyrate [prepared by hydrolysis of the enol esters (535 g) as in Example 1(i)] in absolute ethanol (200 ml) was added and heated at 70°-80° with stirring for 20 hours. After cooling the mixture to room temperature, ammonium chloride was removed by filtration and the filtrate concentrated and diluted with ethyl acetate (250 ml) to precipitate the triazinone (94.0 g). The filtrate on standing deposited a second crop (6.7 g). Two recrystallisations from ethanol gave a sample of m.p. 224°-226°.

Workup

  1. temperaturecooled to 5°
  2. additionwas added
  3. temperatureheated at 70°-80°
  4. stirringwith stirring for 20 hours
  5. customammonium chloride was removed by filtration
  6. concentrationthe filtrate concentrated
  7. additiondiluted with ethyl acetate (250 ml)
  8. customto precipitate the triazinone (94.0 g)
  9. customTwo recrystallisations from ethanol
  10. customgave a sample of m.p. 224°-226°

Sources & evidence

ORD record
ord-3b79598c53764024a7e25f173b8e8018
Source dataset
uspto-grants-1981_07
Patent number
US04278673

Reaction notes

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