4-Aminophenol → 4-(3-Chloropyrazin-2-yloxy)benzenamine

HRID 473634Notes

Reaction equation

HRID 473634 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[Cl:8][C:7]1[C:2]([O:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonateHCID 785752,3-Dichloropyrazine

Product 1

HCID 201339744-(3-Chloropyrazin-2-yloxy)benzenamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a round-bottomed flask was added 2,3-dichloropyrazine (7.3582 g, 49.4 mmol), 4-aminophenol (5.39 g, 49.4 mmol), and cesium carbonate (48.3 g, 148 mmol) in DMSO (165 mL) at 110° C. to stir overnight. The reaction mixture was diluted with water and extracted with EtOAc. The organic extract was washed with water, sat NaCl, sat sodium bicarbonate, dried with magnesium sulfate, filtered, and concentrated to give the title compound. MS (ESI, pos. ion) m/z: 222.1.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-edb4d39bc15145d6914e6f7cba38a022
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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