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

HRID 279951Notes

Reaction equation

[C-:1]#[N:2].[Na+].Cl[C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]=[CH:7][C:6]=1[C:16]([O:18]CC)=O.[CH3:21][NH2:22].O>CN(C=O)C>[C:1]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:8]=[CH:7][C:6]=1[C:16]([NH:22][CH3:21])=[O:18])#[N:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Four and seven tenths grams (0.096 mol) of sodium cyanide were added to a solution of 12.0 g (0.048 mol) of 94.66% pure 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester in 28.8 ml of DMF at room temperature. The solution was heated for 6 hours at 100° C. and cooled to room temperature. The reaction mixture was stirred overnight and 13.0 g (0.17 mol) of 40% aqueous methylamine was added dropwise. The resulting mixture was stirred for 6 hours at room temperature and 28.8 ml of water was slowly added. The mixture was stirred for 10 minutes and the precipitated solid was collected by filtration. This solid was washed with water and vacuum dried to provide 8.3 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide as a white solid. The product analyzed 95.81% pure by high pressure liquid chromatography, corresponding to a corrected yield of 77.4% product.

Workup

temperaturecooled to room temperature
stirringThe resulting mixture was stirred for 6 hours at room temperature
stirringThe mixture was stirred for 10 minutes
filtrationthe precipitated solid was collected by filtration
washThis solid was washed with water and vacuum
customdried

Sources & evidence

ORD record: ord-91491d9b2e5a45b19a5ea7cbc225c8e3
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587348

Reaction notes

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