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

HRID 279955Notes

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+].CS(C)=O.[CH3:25][NH2:26]>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:26][CH3:25])=[O:15])#[N:19]

Participants

Conditions

Temperature: 125 °C

Procedure

A 500 ml 3-neck round bottom flask fitted with a mechanical stirrer was sequentially charged with 40.0 g (0.16 mol) of 5-chloro-1-phenyl-1H-pyrazole-4-carboxylic acid, ethyl ester, 15.68 g (0.32 mol) of sodium cyanide and 96 ml of dimethylsulfoxide. The reaction mixture was heated to about 125° C. and cooled to 100° C., at which temperature the reaction mixture was stirred for 6 hours. The mixture was stirred at room temperature overnight and charged with 43.4 g (0.56 mol) of 40% queous methylamine dropwise. The resulting mixture was stirred for 61/2 hours at room temperature and 96 ml of water was added thereto. The mixture was stirred for one hour and the precipitated solid was collected by vacuum filtration. The resulting solid was washed with water and vacuum dried to afford 27.5 g of 96.19% pure 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. Corrected yield 73.6%.

Workup

customA 500 ml 3-neck round bottom flask fitted with a mechanical stirrer
temperaturecooled to 100° C., at which temperature the reaction mixture
stirringThe mixture was stirred at room temperature overnight
stirringThe resulting mixture was stirred for 61/2 hours at room temperature
stirringThe mixture was stirred for one hour
filtrationthe precipitated solid was collected by vacuum filtration
washThe resulting solid was washed with water and vacuum
customdried

Sources & evidence

ORD record: ord-22d4efbc4514469f8712b136e0cc0bd3
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587348

Reaction notes

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