Potassium Carbonate → HCID 66726170, compound

HRID 1042138Notes

Reaction equation

HRID 1042138 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][S:13]([C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])[O:22][C:19]1[CH:18]=[CH:17][C:16]([S:13]([CH3:12])(=[O:15])=[O:14])=[N:21][CH:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 231451966-(Methylsulfonyl)pyridin-3-ol

Product 1

HCID 66726170HCID 66726170, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-fluoro-2-methyl-1-nitrobenzene (9.4 g), 6-(methylsulfonyl)pyridin-3-ol (10.0 g), potassium carbonate (8.8 g), and N,N-dimethylformamide (100 mL) was stirred at 60° C. for 24 hr. The reaction solution was concentrated under reduced pressure, and the obtained residue was added to a mixture of ethyl acetate-water. The precipitated solid was collected by filtration, washed with water and ethyl acetate and dried to give the title compound (8.28 g) as a pale-yellow solid. The filtrate was extracted with ethyl acetate, washed successively with aqueous citric acid solution, water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (4.30 g) as a pale-yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe obtained residue was added to a mixture of ethyl acetate-water
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-588eff01a21a49cfac49e14bbd8a4576
Source dataset
uspto-grants-2013_10
Patent number
US08557805B2

Reaction notes

Loading…