Hydrochloric Acid → HCID 68553145, compound

HRID 2381972Notes

Reaction equation

HRID 2381972 reaction equation
[C:1]([C:5]1[CH2:6][N:7]([NH:12]C(=O)C)[C:8](=[O:11])[NH:9][N:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[OH-].[Na+]>CO>[NH2:12][N:7]1[CH2:6][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[N:10][NH:9][C:8]1=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68557137HCID 68557137, compound

Product 1

HCID 68553145HCID 68553145, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a slurry of N-(6-tert-butyl-3-oxo-2,5-dihydro-3H-1,2,4-triazin-4-yl)-acetamide (0.51 g, 2.40 mmol) in MeOH (5 mL) is added concentrated HCl (0.33 mL, 3.84 mmol). The mixture is heated to reflux for 3 h. The mixture is then chilled to 0° C. and basified with 1 M aqueous NaOH (2.9 mL) to pH 12, and concentrated in vacuo. EtOH is added to the residue with stirring and the mixture is filtered. The filtrate is concentrated in vacuo. CH3CN is added to the residue with stirring and the mixture is filtered. The filtrate is concentrated in vacuo to afford 4-amino-6-tert-butyl-4,5-dihydro-2H-1,2,4-triazin-3-one (0.354 g, 84%) as a solid. MS: 171 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 7.49 (br s, 1H), 4.22 (br s, 2H), 4.06 (s, 2H), 1.15 (s, 9H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated in vacuo
  4. additionEtOH is added to the residue
  5. filtrationthe mixture is filtered
  6. concentrationThe filtrate is concentrated in vacuo
  7. additionCH3CN is added to the residue
  8. stirringwith stirring
  9. filtrationthe mixture is filtered
  10. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1eaf8d4d9aa7458196f4c44faf37456e
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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