Nitric Acid → HCID 13913350, compound

HRID 986190Notes

Reaction equation

HRID 986190 reaction equation
C(OC(=O)C)(=O)C.[N+:8]([O-:11])(O)=[O:9].[F:12][C:13]([F:36])([F:35])[C:14]([NH:16][C:17]1[N:21]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[C:24]([Cl:33])[C:23]=2[Cl:34])[N:20]=[CH:19][CH:18]=1)=[O:15]>C(O)(=O)C>[N+:8]([C:18]1[CH:19]=[N:20][N:21]([C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[C:24]([Cl:33])[C:23]=2[Cl:34])[C:17]=1[NH:16][C:14](=[O:15])[C:13]([F:36])([F:35])[F:12])([O-:11])=[O:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 13913349HCID 13913349, compound

Product 1

HCID 13913350HCID 13913350, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2.4 ml (0.0258 mol) of acetic anhydride and 1.1 ml (0.025 mol) of 98% strength nitric acid are added in succession to 10 g (0.0235 mol) of 5-trifluoroacetamido-1-(2,3,6-trichloro-4-trifluoromethylphenyl)-pyrazole in 20 ml of glacial acetic acid at room temperature. After the mixture has been stirred for 20 hours, it is concentrated in vacuo, the residue is taken up in 100 ml of methylene chloride and the mixture is extracted with 400 ml of 5% strength aqueous sodium carbonate solution. The aqueous phase is acidified and extracted with 200 ml of methylene chloride. The combined organic phases are dried over magnesium sulphate and freed from the solvent in vacuo. 8.6 g (77.6% of theory) of 4-nitro-5-trifluoroacetamido-1-(2,3,6-trichloro-4-trifluoromethylphenyl)-pyrazole of melting point 136° C.-137° C. are obtained.

Workup

  1. concentrationit is concentrated in vacuo
  2. extractionthe mixture is extracted with 400 ml of 5% strength aqueous sodium carbonate solution
  3. extractionextracted with 200 ml of methylene chloride
  4. dry with materialThe combined organic phases are dried over magnesium sulphate

Sources & evidence

ORD record
ord-1c41912623024b80b66d1202b5b83344
Source dataset
uspto-grants-1987_12
Patent number
US04711658

Reaction notes

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