Cesium carbonate → HCID 58158548, compound

HRID 2095756Notes

Reaction equation

HRID 2095756 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[OH:8].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[N:31][CH:32]=1.C(=O)([O-])O.[Na+]>CS(C)=O.O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:27]1[CH:32]=[N:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2598065-Chloro-2-nitropyridineHCID 516892Sodium BicarbonateHCID 58158634HCID 58158634, compound

Product 1

HCID 58158548HCID 58158548, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of benzyl (3-fluoro-4-hydroxyphenyl)carbamate (80 g, 252 mmol) in dimethyl sulfoxide (600 mL) were added cesium carbonate (123 g, 378 mmol) and 5-chloro-2-nitropyridine (40 g, 252 mmol), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate (1000 mL) and water (1000 mL) were added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=3/1) and collected by filtration to give the title compound (79.8 g, 83%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with hexane/ethyl acetate (=3/1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-24ec7688bb4c4f1e9b2fa9507fde4560
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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