Cesium carbonate → HCID 86630117, compound

HRID 1715313Notes

Reaction equation

HRID 1715313 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O.[Cl:14][C:15]1[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][N:16]=1.Cl[C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH2:32][CH3:33])(=[O:31])=[O:30])=[N:27][CH:28]=1>C(OCC)(=O)C.[Cl-].[NH4+]>[Cl:14][C:15]1[C:20]([O:21][C:23]2[CH:28]=[N:27][C:26]([S:29]([CH2:32][CH3:33])(=[O:30])=[O:31])=[CH:25][CH:24]=2)=[CH:19][CH:18]=[CH:17][N:16]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 811362-Chloro-3-pyridinolHCID 231451535-Chloro-2-(ethanesulfonyl)pyridine

Product 1

HCID 86630117HCID 86630117, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (20 g) was added to an N-methyl-2-pyrrolidinone (160 ml) solution of 2-chloro-3-hydroxypyridine (6 g) and 5-chloro-2-(ethylsulfonyl)pyridine (4.8 g), and stirred at 100° C. for 24 hours. After this was diluted with ethyl acetate, aqueous saturated ammonium chloride solution was added with cooling with ice. The organic layer was washed with water and saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the entitled compound as a brown oil.

Workup

  1. additionwas added
  2. temperaturewith cooling with ice
  3. washThe organic layer was washed with water and saturated saline water
  4. customAfter dried
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ec09882111ee49139e4d4cf6afd797be
Source dataset
uspto-grants-2010_09
Patent number
US07799820B2

Reaction notes

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