Dimethylformamide → 1H-Pyrazole-4-carboxamide, 5-cyano-N-methyl-1-phenyl-

HRID 279953Notes

Reaction equation

Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15]CC)=O.[C-:18]#[N:19].[Na+].C[N:22]([CH:24]=O)C.CN>O>[C:18]([C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:5]=[CH:4][C:3]=1[C:13]([NH:22][CH3:24])=[O:15])#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 25.4 g (0.1 mol) of 96.17% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester, 9.8 g (0.2 mol) of sodium cyanide and 75 ml of DMF was heated at 100° C. for 6 hours. The mixture was cooled and stirred for 17 hours at room temperature. A solution of 27.13 g (0.35 mol) of 40% aqueous methylamine was added dropwise to the reaction mixture over a 5 minute period, and the resulting mixture was stirred at room temperature for 22 hours. Seventy-five milliliters of water were added and the reaction mixture was stirred at room temperature for approximately 1 hour. The precipitate was collected by filtration and vacuum dried to afford 19.4 g of 5-cyano-1-phenyl-N-methy-1H-pyrazole-4-carboxamide. Purity of this material as determined by high pressure liquid chromatography was 98.5%. The corrected yield of the product was 87.9%.

Workup

temperatureThe mixture was cooled
stirringthe resulting mixture was stirred at room temperature for 22 hours
stirringthe reaction mixture was stirred at room temperature for approximately 1 hour
filtrationThe precipitate was collected by filtration and vacuum
customdried

Sources & evidence

ORD record: ord-b31bea582da64c9ca92c4c7dab2be81c
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587348

Reaction notes

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