Bromoform → HCID 22618615, compound

HRID 861234Notes

Reaction equation

HRID 861234 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[N+:28]([O-:30])=[O:29].C(Br)(Br)[Br:32]>C(#N)C>[Br:32][C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[N+:28]([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 5558BromoformHCID 10906Tert-Butyl nitriteHCID 22618418HCID 22618418, compound

Product 1

HCID 22618615HCID 22618615, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Tertiary butyl nitrite (6.6 ml) was added at room temperature to a solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-nitropyrazole (3.7 g), bromoform (13.3 ml) and acetonitrile (10 ml). The mixture was heated at 50°-60° C. for 4.5 hours and the solvents were evaporated to give an orange oil. This was purified by medium pressure liquid chromatography (eluant hexane/ether 2:1) to give 5-bromo-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-nitropyrazole (3.4 g) as a solid, m.p. 147°-150° C.

Workup

  1. temperatureThe mixture was heated at 50°-60° C. for 4.5 hours
  2. customthe solvents were evaporated
  3. customto give an orange oil
  4. customThis was purified by medium pressure liquid chromatography (eluant hexane/ether 2:1)

Sources & evidence

ORD record
ord-bcf5c27bd6e14ba8a5d33c79ac438a00
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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