Cesium carbonate → HCID 86657976, compound

HRID 2366806Notes

Reaction equation

HRID 2366806 reaction equation
[OH: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[CH3:8].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][N:28]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][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:3][C:2]=1[O:1][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][N:28]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 783082-Chloro-5-nitropyridineHCID 86657975HCID 86657975, compound

Product 1

HCID 86657976HCID 86657976, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl (3-hydroxy-4-methylphenyl)carbamate (83.1 g, 321 mmol) in N,N-dimethylformamide (300 mL) were added cesium carbonate (157 g, 482 mmol) and 2-chloro-5-nitropyridine (50.9 g, 321 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with water (1 L), and the obtained aqueous layer was extracted with ethyl acetate (2×200 mL). The combined organic layer was washed with saturated brine (100 mL) and purified by basic silica gel (ethyl acetate). The obtained solution was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate/hexane (1:1) to give the title compound (91.8 g, 75%) as a pale-yellow solid.

Workup

  1. washwashed with water (1 L)
  2. extractionthe obtained aqueous layer was extracted with ethyl acetate (2×200 mL)
  3. washThe combined organic layer was washed with saturated brine (100 mL)
  4. custompurified by basic silica gel (ethyl acetate)
  5. concentrationThe obtained solution was concentrated under reduced pressure
  6. washThe obtained residue was washed with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record
ord-01f9d79a295a4fc89f77b88ec4dd54a9
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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