Hydrazine hydrate (1:1) → N-(6-Methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl)acetamide

HRID 1110108Notes

Reaction equation

HRID 1110108 reaction equation
[CH3:1][C:2]1[O:6][C:5](=[O:7])[N:4]([CH2:8][C:9](=O)[CH3:10])[N:3]=1.O.[NH2:13][NH2:14].O.O.C(O)(=O)C(O)=O>C(O)(C)C.O>[C:2]([NH:3][N:4]1[CH2:8][C:9]([CH3:10])=[N:14][NH:13][C:5]1=[O:7])(=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 61373Oxalic acid dihydrateHCID 110409205-Methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 11008343N-(6-Methyl-3-oxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a solution of 156 g of 2,3-dihydro-5-methyl-2-oxo-1,3,4-oxadiazol-3-ylacetone in 600 ml of isopropanol and 15 ml of water, 75 g of hydrazine hydrate are added at 70° C. over a period of 30 minutes. The mixture is subsequently stirred at reflux temperature for a further 6 hours. 40 g of oxalic acid dihydrate in 160 ml of isopropanol are added, and the precipitate is filtered off, while the mixture is hot, and washed with 150 ml of isopropanol. The filtrate is evaporated in vacuo until the total volume is about 600 ml, then cooled to 0° C. to +5° C., and the precipitated product is filtered off and dried yielding 158 g (93% of the theoretical amount) of the title compound having a melting point of 199°-200° C.

Workup

  1. temperatureat reflux temperature for a further 6 hours
  2. filtrationthe precipitate is filtered off, while the mixture
  3. washwashed with 150 ml of isopropanol
  4. customThe filtrate is evaporated in vacuo until the total volume is about 600 ml
  5. temperaturecooled to 0° C. to +5° C.
  6. filtrationthe precipitated product is filtered off
  7. customdried

Sources & evidence

ORD record
ord-a588ecead0d744089c4f4776266b61d6
Source dataset
uspto-grants-1994_06
Patent number
US05324842

Reaction notes

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