Nitric Acid → HCID 18355378, compound

HRID 429319Notes

Reaction equation

HRID 429319 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][CH:20]=[C:19]([O:23][CH3:24])[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:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:14])=[O:15])=[CH:9][CH:8]=2)[N:4]([C:17]2[CH:22]=[CH:21][C:20]([N+:25]([O-:27])=[O:26])=[C:19]([O:23][CH3:24])[CH:18]=2)[N:3]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 9799089HCID 9799089, compound

Product 1

HCID 18355378HCID 18355378, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-chloro-1-(3-methoxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (575 mg) in acetic anhydride (10 ml) and acetic acid (1 ml) was added nitric acid (fuming) (500 ml) at 0° C. After being stirred at 0° C. for 2 hours, the reaction mixture was poured into water, and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, and filtered. The filtrate was evaporated in vacuo, and purified by column chromatography using dichloromethane as eluent to give 3-chloro-1-(3-methoxy-4-nitro-phenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole (590 mg).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-c4ff6d7166474100a67d9d6b3e63c91d
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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