Water → HCID 58158630, compound

HRID 2095762Notes

Reaction equation

HRID 2095762 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.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.O>CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([O:8][C:27]2[CH:32]=[N:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2598065-Chloro-2-nitropyridineHCID 58158451HCID 58158451, compound

Product 1

HCID 58158630HCID 58158630, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of benzyl (2-fluoro-4-hydroxyphenyl)carbamate (79 g, 303 mmol) in dimethyl sulfoxide (480 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 6 hr. Water (1000 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The 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 (74 g, 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe 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-49883d04fbc44b82b7daad114cf461a8
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

Loading…