p-Fluoronitrobenzene → HCID 18677105, compound

HRID 1634128Notes

Reaction equation

HRID 1634128 reaction equation
[CH3:1][S:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:4]=1.CC(C)([O-])C.[K+].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>CS(C)=O.O>[CH3:1][S:2][C:3]1[N:7]([C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)[N:6]=[C:5]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:4]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxideHCID 178503085HCID 178503085, compound

Product 1

HCID 18677105HCID 18677105, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of the above pyrazole(1.94 g, 10.15 mmol) and potassium t-butoxide (1.2 g, 10.6 mmol) in anhydrous DMSO (15 mL) was stirred at room temperature for 5 min and then 4-flouronitrobenzene (1.08 mL, 10.15 mmol) was added. The reaction mixture was heated to 100° C. in an oil bath for 5 h under argon. The reaction mixture was cooled, diluted with water, the yellow solid obtained was filtered, washed with water and dried. The residue obtained was recrystallized from ethyl acetate to give 5-methylthio-1-(4-nitrophenyl)-3-(3-pyridinyl)pyrazole (2.4 g).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe yellow solid obtained
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried
  6. customThe residue obtained
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ca27f86923684b96b81e7a75f3caa41b
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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