Nitric Acid → 5-Cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-nitro-pyrazole

HRID 622607Notes

Reaction equation

HRID 622607 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].C(OC(=O)C)(=O)C.[N+:31]([O-])([OH:33])=[O:32]>C(O)(=O)C>[C:1]([CH2:3][C:4]([NH:6][C:7]1[N:11]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:20])([F:22])[F:21])=[CH:14][C:13]=2[Cl:23])[N:10]=[CH:9][C:8]=1[N+:31]([O-:33])=[O:32])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 139850675-Cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole

Product 1

HCID 139850685-Cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-nitro-pyrazoleYield 36%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.26 g (0.02 mol) of 5-cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-pyrazole (Example 1) are taken in 70 ml of glacial acetic acid, and 2 ml of acetic anhydride and 2 ml of nitric acid are added dropwise in succession at about 10° C. A crystalline solid precipitates out of the initially clear solution after prolonged stirring. After filtration with suction, washing several times with diisopropyl ether and drying, 2.9 g (36% of theory) of 5-cyanoacetylamino-1-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-nitro-pyrazole of melting point 221°-223° C. are obtained.

Workup

  1. customA crystalline solid precipitates out of the initially clear solution
  2. filtrationAfter filtration with suction
  3. washwashing several times with diisopropyl ether
  4. customdrying

Sources & evidence

ORD record
ord-66cb4facf573415587a386fcd5e8c7cc
Source dataset
uspto-grants-1988_09
Patent number
US04772310

Reaction notes

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