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

HRID 887403Notes

Reaction equation

HRID 887403 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>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,3-dichloropyrazine (470 mg, 3155 μmol) was combined with 4-aminophenol (344 mg, 3155 μmol) and cesium carbonate (1233 mg, 3786 μmol) in DMSO (5 ml) and heated to 70 C. After 3 hours, the mixture was cooled to room temperature, transferred to a separatory funnel rinsing with ethyl acetate and water, the layers were separated and the aqueous was extracted with ethyl acetate (3×). The combined organics were rinsed with brine, dried over sodium sulfate, filtered and concentrated to yield a brown solid which was carried forward without purification.

Workup

  1. temperatureheated to 70 C
  2. customtransferred to a separatory funnel
  3. washrinsing with ethyl acetate and water
  4. customthe layers were separated
  5. extractionthe aqueous was extracted with ethyl acetate (3×)
  6. washThe combined organics were rinsed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a brown solid which
  11. customwas carried forward without purification

Sources & evidence

ORD record
ord-0d6f30d2771542fdaaa7b0cb39bc45b2
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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