Sodium Hydroxide → HCID 136365713, compound

HRID 705037Notes

Reaction equation

HRID 705037 reaction equation
N[N:2]1[C:6]([CH3:7])=[N:5][N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]1=[O:14].N([O-])=O.[Na+].[OH-].[Na+]>O.Cl.S(=O)(O)[O-].[Na+]>[CH3:7][C:6]1[NH:2][C:3](=[O:14])[N:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 67516508HCID 67516508, compound

Product 1

HCID 136365713HCID 136365713, compound

Reagents, catalysts & solvents 3

HCID 23665763Sodium BisulfiteCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

750 mg (3.923 mmol) of 4-amino-5-methyl-2-(pyridin-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one were dissolved in a mixture of 9 ml of water and 3 ml of concentrated hydrochloric acid. At 5° C., a solution of 314 mg (4.55 mmol) of sodium nitrite in 1 ml of water was then added dropwise. The reaction mixture was then allowed to warm to room temperature and stirred for another 1 hour. The reaction mixture was neutralized using 30% strength aqueous sodium hydroxide solution and a few drops of an aqueous sodium bisulfite solution were added such that the test with potassium iodide/starch paper is negative. The mixture was extracted repeatedly with ethyl acetate, and the combined organic phases were dried with sodium sulfate and concentrated. This gave 253 mg of 5-methyl-2-(pyridin-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one in the form of a white solid (content LC-MS: 100%) which was used for the next reaction.

Workup

  1. extractionThe mixture was extracted repeatedly with ethyl acetate
  2. dry with materialthe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated
  4. customThis gave 253 mg of 5-methyl-2-(pyridin-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one in the form of a white solid (content LC-MS: 100%) which was used for the next reaction

Sources & evidence

ORD record
ord-f66eda66ad9e4fe5985325ae030a766b
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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