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Trifluoroacetic anhydride → Ethyl 3-methyl-4-nitro-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylate

HRID 598194
Notes
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Reaction equation

HRID 598194 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([Cl:19])=[CH:14][C:13]=2[Cl:20])[N:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[N+:34]([O-])([O-:36])=[O:35].[NH4+].C(=O)([O-])[O-].[K+].[K+]>FC(F)(F)C(O)=O>[CH3:1][C:2]1[C:6]([N+:34]([O-:36])=[O:35])=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:4]([C:12]2[C:13]([Cl:20])=[CH:14][C:15]([Cl:19])=[CH:16][C:17]=2[Cl:18])[N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 11430Potassium CarbonateHCID 22985Ammonium nitrateHCID 67267631Ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 67267347Ethyl 3-methyl-4-nitro-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylateYield 66%

Reagents, catalysts & solvents

1
HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of ethyl 3-methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazole-5-carboxylate (500 mg, 1.50 mmol) in trifluoroacetic acid (2.54 ml) was added trifluoroacetic anhydride (1.48 ml) followed by an addition of ammonium nitrate (240 mg, 3.00 mmol). The mixture was stirred for 20 h at room temperature and neutralized with aqueous potassium carbonate. The aqueous solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with 3% ethyl acetate/n-hexane to give the title compound (372 mg, 66%).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate
  2. dry with materialThe extract was dried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 3% ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-9f8ef8f3eb3645bcb0d124d64ef7ba50
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897607B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes