Oxalic Acid → HCID 68557069, compound

HRID 2381968Notes

Reaction equation

HRID 2381968 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.[CH3:12][NH:13][NH2:14].C(O)(=O)C(O)=O>CC(O)C.O>[CH3:12][N:13]1[C:5](=[O:7])[N:4]([NH:3][C:2](=[O:6])[CH3:1])[CH2:8][C:9]([CH3:10])=[N:14]1

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 6061MethylhydrazineHCID 110409205-Methyl-3-(2-oxopropyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 68557069HCID 68557069, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a solution of 5-methyl-3-(2-oxo-propyl)-3H-1,3,4-oxadiazol-2-one (1.518 g, 9.72 mmol) in a mixture of 2-propanol (8.8 mL) and water (0.22 mL) is added methyl hydrazine (0.79 mL, 14.6 mmol). The reaction mixture is heated to reflux under N2 for 4 h, and then a solution of oxalic acid (0.273 g, 2.92 mmol) in 2-propanol (4 mL) is added. The resulting precipitate is removed by filtration. The filtrate is concentrated in vacuo and the residue dissolved in 2-propanol (25 mL). The solution is chilled and Et2O is added. The precipitate is collected by filtration and dried to afford N-(2,6-dimethyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-acetamide (0.96 g, 54%) as a crystalline solid. MS: 185 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 8.28 (s, 1H), 4.18 (s, 2H), 3.28 (s, 3H), 2.02 (s, 3H), 1.95 (s, 2H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under N2 for 4 h
  3. customThe resulting precipitate is removed by filtration
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue dissolved in 2-propanol (25 mL)
  6. temperatureThe solution is chilled
  7. additionEt2O is added
  8. filtrationThe precipitate is collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-62d135c2e1494c52957ec7a90ef32d32
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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