Potassium Carbonate → N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amine

HRID 732096Notes

Reaction equation

HRID 732096 reaction equation
[NH2:1][NH:2][C:3]([NH:6][CH3:7])=[N:4][CH3:5].Cl.[C:9](Cl)(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[N:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[CH3:7][NH:6][C:3]1[N:4]([CH3:5])[C:9]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[N:1][N:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 415738N-amino-N',N''-dimethyl-guanidine

Product 1

HCID 57837974N,4-dimethyl-5-pyridin-3-yl-4H-1,2,4-triazol-3-amine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of N-amino-N′,N″-dimethyl-guanidine (500 mg, 2.17 mmol) [J. Amer. Chem. Soc.; 1951; p. 1858] and nicotinoyl chloride hydrochloride (385 mg, 2.17 mmol) in pyridine (10 mL) was refluxed o.n. Aq. sat. K2CO3 was added and the mixture extracted with CHCl3. The organic phase was dried and concentrated. The crude product 240 mg (61%) was used in the next step without further purifications.

Workup

  1. temperaturewas refluxed o.n
  2. extractionthe mixture extracted with CHCl3
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55d2d62ef1dd417c82885a35736ed1dc
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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