Water → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-oximinomethylpyrazole

HRID 377649Notes

Reaction equation

HRID 377649 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[CH:21]=O.Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+].O>C(O)C>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[CH:21]=[N:24][OH:25]

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 193564785-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-formylpyrazole

Product 1

HCID 867551545-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-oximinomethylpyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-formylpyrazole (0.25 g) in ethanol (3 ml) was added hydroxylamine hydrochloride (0.075 g), sodium acetate (0.1 g) and water (0.1 ml). After stirring at room temperature overnight the mixture was evaporated. The residue was taken up in ether and washed with water, then brine, then dried and evaporated. The residue was crystallised from propan-2-ol/water and further purified by column chromatography on silica gel eluted with dichloromethane then dichloromethane:methanol (99:1). After combination and evaporation of suitable fractions the residue was further purified by column chromatography on silica gel eluted with ether. Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p. 175-178° C.

Workup

  1. customwas evaporated
  2. washwashed with water
  3. dry with materialbrine, then dried
  4. customevaporated
  5. customThe residue was crystallised from propan-2-ol/water
  6. customfurther purified by column chromatography on silica gel
  7. washeluted with dichloromethane
  8. customAfter combination and evaporation of suitable fractions the residue
  9. customwas further purified by column chromatography on silica gel
  10. washeluted with ether
  11. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-0623b8bde38c4100b3103928bdb47ce8
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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