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

HRID 473680Notes

Reaction equation

HRID 473680 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+].O>CS(C)=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 4

HCID 4034-AminophenolHCID 962WaterHCID 10796Cesium carbonateHCID 785752,3-Dichloropyrazine

Product 1

HCID 201339744-(3-Chloropyrazin-2-yloxy)benzenamineYield 79%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,3-Dichloropyrazine (2.67 mL, 25.6 mmol), 4-aminophenol (2.29 g, 21 mmol), and cesium carbonate (8.21 g, 25.2 mmol) in dimethyl sulfoxide (70 mL) under argon was stirred at 100° C. for 18 h. The cooled reaction mixture was poured into water (100 mL), resulting in the precipitation of a brick-colored solid. After stirring for 10 min, the brown slurry was filtered to give a relatively pure crop of 4-(3-chloropyrazin-2-yloxy)aniline (3.67 g, 79% yield) as a brick-colored solid. [M+1]=222.1.

Workup

  1. customThe cooled reaction mixture
  2. customresulting in the precipitation of a brick-colored solid
  3. filtrationthe brown slurry was filtered

Sources & evidence

ORD record
ord-855c596043b34f678e09ea2329f166ea
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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