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

HRID 280460Notes

Reaction equation

Br[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]([NH:15][CH3:16])=[O:14].[C-:17]#[N:18].[Na+]>CN(C=O)C>[C:17]([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]([NH:15][CH3:16])=[O:14])#[N:18]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 5.6 g of 5-bromo-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide and 2 g of sodium cyanide in 30 ml of DMF was heated at approximately 100° C. for 24 hours. An additional 2 g of sodium cyanide was next added to the reaction mixture which was then heated for an additional 24 hours at 100° C. The solution was poured into ice water and the precipitated solid was collected by filtration. The product thus isolated was recrystallized from 3A ethanol to provide 1.8 g of 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide. MP=203°-204° C.

Workup

filtrationthe precipitated solid was collected by filtration
customThe product thus isolated
customwas recrystallized from 3A ethanol

Sources & evidence

ORD record: ord-16aab29010504888b058a2fda4dd0be5
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04589905

Reaction notes

Loading…