Tert-Butyl nitrite → 4-Acetyl-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)pyrazole

HRID 377664Notes

Reaction equation

HRID 377664 reaction equation
[C:1]([C:4]1[C:5]([C:23]#[N:24])=[N:6][N:7]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[Cl:22])[C:8]=1N)(=[O:3])[CH3:2].C(ON=O)(C)(C)C>O1CCCC1>[C:1]([C:4]1[C:5]([C:23]#[N:24])=[N:6][N:7]([C:10]2[C:15]([Cl:16])=[CH:14][C:13]([O:17][C:18]([F:19])([F:21])[F:20])=[CH:12][C:11]=2[Cl:22])[CH:8]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 193564804-Acetyl-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)pyrazole

Product 1

HCID 193564794-Acetyl-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-acetyl-5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethoxyphenyl)pyrazole (0.302 g) in tetrahydrofuran (10 ml) at 2° C. was added t-butylnitrite (0.66 ml). The mixture was heated under reflux for 1.5 hours and then evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane. Combination and evaporation of suitable fractions provided the title compound as a white solid, m.p. 105.7-106.6° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with dichloromethane
  6. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-7c09078dd64c4beca4c39a7f7edeabe0
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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