Nitric Acid → HCID 9953232, compound

HRID 429330Notes

Reaction equation

HRID 429330 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[N:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:3]=1.[N+:25]([O-])([OH:27])=[O:26].O>C(OC(=O)C)(=O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:11][CH:12]=2)[N:4]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([N+:25]([O-:27])=[O:26])[CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 18355394HCID 18355394, compound

Product 1

HCID 9953232HCID 9953232, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

To a stirred solution of 3-chloro-1-(4-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (278 mg) in a mixture of acetic anhydride (5 ml) and acetic acid (5 ml), nitric acid (sp. gr. 1.42) (0.5 ml) was added at 0° C. After 30 minutes, the resulting mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure to give crystals. The resulting crystals were washed with ethyl acetate to give 3-chloro-1-(4-methoxy-3-nitro-phenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (297 mg).

Workup

  1. additionwas added at 0° C
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crystals
  7. washThe resulting crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-d3ff5d1cf2f9447e8916d7d8d94b11fc
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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