Isoamyl Nitrite → HCID 13537966, compound

HRID 1284400Notes

Reaction equation

HRID 1284400 reaction equation
N[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]#[N:16].[Br:17]Br.N(OCCC(C)C)=O>C(Cl)(Cl)Cl>[Br:17][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]#[N:16]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 24408BromineHCID 1736451H-pyrazole-4-carbonitrile, 5-amino-1-(2,4-dichlorophenyl)-

Product 1

HCID 13537966HCID 13537966, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-amino-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbonitrile and 3 ml of bromine in 50 ml of chloroform was added 1.7 g of isoamyl nitrite. The reaction mixture was stirred at room temperature for approximately 10 minutes and then refluxed for approximately one hour. The solution was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel employing toluene as the eluent. Fractions containing the major component were combined and the solvent was evaporated therefrom to afford 0.8 g of 5-bromo-1-(2,4-dichlorophenyl)-1H-pyrazole-4-carbonitrile after crystallization from 3A alcohol. mp=101°-102° C.

Workup

  1. temperaturerefluxed for approximately one hour
  2. customThe solution was evaporated to dryness under reduced pressure
  3. customthe residue was chromatographed over silica gel
  4. additionFractions containing the major component
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7937f5ddb8844cad8f59dce761d150a3
Source dataset
uspto-grants-1986_01
Patent number
US04563210

Reaction notes

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