Phenol → HCID 23092606, compound

HRID 1616522Notes

Reaction equation

HRID 1616522 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:14][C:15]1[C:16]([C:22]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:17][C:18](Cl)=[CH:19][CH:20]=1.[OH-].[Na+]>CN(C)C=O>[Cl:14][C:15]1[C:16]([C:22]([NH:24][C:25]2[S:26][CH:27]=[C:28]([CH3:30])[N:29]=2)=[O:23])=[N:17][C:18]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 23092625HCID 23092625, compound

Product 1

HCID 23092606HCID 23092606, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Phenol (135 mg; 1.43 mmol) and 540 mg (1.66 mol) of cesium carbonate were added to a solution (3 ml) of 84 mg (0.292 mmol) of 3,6-dichloro-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide in N,N-dimethylformamide followed by stirring at 120° C. for 24 hours. Aqueous solution (1N) of sodium hydroxide was added to the reaction solution followed by extracting with ethyl acetate. The organic layer was washed with water and a saturated aqueous saline solution, dried and concentrated in vacuo. The resulting residue was purified by a thin-layer silica gel chromatography (hexane:ethyl acetate=4:1) to give 61 mg (yield: 61%) of 3-chloro-6-phenoxy-N-(4-methyl-thiazole-2-yl)-2-pyridine carboxamide as a white solid.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe organic layer was washed with water
  3. customa saturated aqueous saline solution, dried
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by a thin-layer silica gel chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-29f6f96ce2ac463696f404266333c217
Source dataset
uspto-grants-2014_07
Patent number
US08765789B2

Reaction notes

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