Lithium cyanide → HCID 13772947, compound

HRID 1249439Notes

Reaction equation

HRID 1249439 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16].[C-:20]#[N:21].[Li+]>CN(C=O)C>[C:20]([C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:5]=[CH:4][C:3]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:21]

Participants

4

Reactant 2

HCID 75478Lithium cyanide2×HCID 867411705-chloro-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester

Product 1

HCID 13772947HCID 13772947, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.4 g of 5-chloro-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester and 2 g of lithium cyanide dissolved in 30 ml of DMF was reacted at approximately 110° C. for 23 hours. One additional gram of lithium cyanide was added to the reaction mixture which was heated for an additional 7 hours. The mixture was poured into ice water and the precipitated solid was collected by filtration and recrystallized from 3A alcohol (charcoal) to provide 3.75 g of 5-cyano-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carboxylic acid, ethyl ester. Yield 61%. mp=79°-81° C.

Workup

  1. customwas reacted at approximately 110° C. for 23 hours
  2. temperaturewas heated for an additional 7 hours
  3. filtrationthe precipitated solid was collected by filtration
  4. customrecrystallized from 3A alcohol (charcoal)

Sources & evidence

ORD record
ord-c4d85b6d1ef74dcbaae99666e91e5ef7
Source dataset
uspto-grants-1986_12
Patent number
US04631343

Reaction notes

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