Ammonia → HCID 86698141, compound

HRID 705036Notes

Reaction equation

HRID 705036 reaction equation
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][C:9]1[N:10]([N:15]=C(CC(C)C)C)[C:11](=[O:14])[NH:12][N:13]=1.[C:22](=O)([O-])[O-].[K+].[K+].N1CC(=O)NN=1.N>CN(C)C=O.[Cu]I.O>[NH2:15][N:10]1[C:9]([CH2:8][CH3:22])=[N:13][N:12]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[C:11]1=[O:14]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 707143-IodopyridineHCID 211131441,2,3-Triazol-5(4)-oneHCID 53800217HCID 53800217, compound

Product 1

HCID 86698141HCID 86698141, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

For 20 min, a weak stream of argon was passed through a mixture of 1.23 g (6.0 mmol) of 3-iodopyridine, 981 mg (5.0 mmol) of 5-methyl-4-[(4-methylpentan-2-ylidene)amino]-2,4-dihydro-3H-1,2,4-triazol-3-one (preparation cf. EP 511569, WO 1993/004050) and 1.037 g (7.5 mmol) of powdered potassium carbonate in 5 ml of N,N-dimethylformamide. 205 mg (1.0 mmol) of copper(I) iodide were then added, and under protective gas the mixture was heated at 150° C. for 2 hours. Analytically, by thin-layer chromatography, no more triazolinone starting material was found. With stirring, 5 ml of 25% strength ammonia solution and 10 ml of water were added to the cooled reaction mixture, which was then extracted three times in each case with 20 ml of ethyl acetate.

Workup

  1. extractionwas then extracted three times in each case with 20 ml of ethyl acetate

Sources & evidence

ORD record
ord-12dbd398048e4efcb1783bccfaf5f2cd
Source dataset
uspto-grants-2015_11
Patent number
US09173396B2

Reaction notes

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