Water → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoroacetylpyrazole

HRID 377665Notes

Reaction equation

HRID 377665 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[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23].[C:27](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[C:19]([C:4]1[C:3]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])=[C:2]([NH:1][CH3:27])[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=1)#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

Product 1

HCID 193564703-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoroacetylpyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole (1 g) in anhydrous N,N-dimethylformamide (5 ml) at room temperature was added potassium carbonate (0.69 g), then iodomethane (97 μl). The mixture was stirred at room temperature for one hour. Water (30 ml) was then added, and the mixture was extracted with ether (50 ml, ×2). The combined organic layers were washed with water (30 ml, ×2), and evaporated. The residue was purified by column chromatography on silica gel (50 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p 160-161° C.

Workup

  1. extractionthe mixture was extracted with ether (50 ml, ×2)
  2. washThe combined organic layers were washed with water (30 ml, ×2)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (50 g)
  5. washeluted with dichloromethane
  6. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-621092639a1e41c6addde6a015662308
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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