Oxalic Acid → HCID 68557137, compound

HRID 2381971Notes

Reaction equation

HRID 2381971 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C:3](=O)[CH2:4][N:5]1[N:9]=C[O:7][C:6]1=O.O.[NH2:15][NH2:16].[C:17]([OH:22])(=O)[C:18](O)=O>CC(O)C.O>[C:2]([C:3]1[CH2:4][N:5]([NH:9][C:17](=[O:22])[CH3:18])[C:6](=[O:7])[NH:15][N:16]=1)([CH3:13])([CH3:12])[CH3:1]

Participants

6

Reactant 3

HCID 971Oxalic AcidHCID 24654Hydrazine hydrate (1:1)HCID 68556783HCID 68556783, compound

Product 1

HCID 68557137HCID 68557137, compoundYield 186.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

To a solution of 3-(3,3-dimethyl-2-oxo-butyl)-3H-1,3,4-oxadiazol-2-one (0.91 g, 4.59 mmol) in a mixture of 2-propanol (4 mL) and water (0.11 mL) is added hydrazine monohydrate (0.34 mL, 6.89 mmol). The reaction mixture is heated to reflux under nitrogen for 5 h, then a solution of oxalic acid (0.13 g, 1.38 mmol) in 2-propanol (5 mL) is added to the hot solution. The resulting precipitate is removed hot by filtration. The filtrate is concentrated in vacuo and the residue is purified on a pad of silica gel, eluting with heptane:EtOAc gradient to afford N-(6-tert-butyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-acetamide (0.546 g, 56%) as a solid. MS: 213 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 8.29 (s, 1H), 7.64 (s, 1H), 4.22 (s, 2H), 2.04 (s, 3H), 1.15 (s, 9H).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux under nitrogen for 5 h
  3. customThe resulting precipitate is removed hot by filtration
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue is purified on a pad of silica gel
  6. washeluting with heptane

Sources & evidence

ORD record
ord-4f9ed92cc2e24e9096c9e2b4776203b4
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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