Water → HCID 59072103, compound

HRID 1042127Notes

Reaction equation

HRID 1042127 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][S:12]([C:15]1[N:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:19][N:20]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 231451966-(Methylsulfonyl)pyridin-3-ol

Product 1

HCID 59072103HCID 59072103, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-fluoronitrobenzene (4.74 g) and 6-(methylsulfonyl)pyridin-3-ol (6.4 g) in N,N-dimethylformamide (50 mL) was added potassium carbonate (9.3 g), and the mixture was stirred at 100° C. for 3 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained crude product was crystallized from diethyl ether to give the title compound (9.88 g, yield 100%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product
  7. customwas crystallized from diethyl ether

Sources & evidence

ORD record
ord-0a2358ed7cf04f8e80e2c4573a750157
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

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