Potassium Carbonate → 6,7-Dichloro-2-isopropyl-3-(4-methylthiazol-2-ylsulfinyl)quinoxaline

HRID 584669Notes

Reaction equation

HRID 584669 reaction equation
[CH:1]([C:4]1[C:5](Cl)=[N:6][C:7]2[C:12]([N:13]=1)=[CH:11][C:10]([Cl:14])=[C:9]([Cl:15])[CH:8]=2)([CH3:3])[CH3:2].[CH3:17][C:18]1[N:19]=[C:20]([SH:23])[S:21][CH:22]=1.C(=O)([O-])[O-:25].[K+].[K+].C1C=C(Cl)C=C(C(OO)=O)C=1>CN(C=O)C>[Cl:15][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[Cl:14])[N:13]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]([S:23]([C:20]1[S:21][CH:22]=[C:18]([CH3:17])[N:19]=1)=[O:25])=[N:6]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 223410512,6,7-Trichloro-3-isopropylquinoxalineHCID 1784319804-methyl-1,3-thiazole-2-thiol

Product 1

HCID 223411416,7-Dichloro-2-isopropyl-3-(4-methylthiazol-2-ylsulfinyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-isopropyl-2,6,7-trichloroquinoxaline (100 mg, 0.364 mmol) in DMF (3 ml) was added 4-methylthiazole-2-thiol (45 mg, 0.38 mmol) followed by potassium carbonate (106 mg, 0.728 mmol). After stirring at room temperature for 5 hours, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate one more time. The combined organic layers were concentrated to dryness. This residue was dissolved in dichloromethane (3 ml). To this solution was added mCPBA (157 mg, 0.73 mmol, 79% pure). The reaction mixture was stirred overnight at room temperature. The reaction was quenched by addition of a saturated solution of sodium bicarbonate. After separating the layers, the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and concentrated under reduced pressure yielding a white solid. This solid was further purified by column chromatography affording two components as a white solid.

Workup

  1. customthe reaction mixture was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate one more time
  4. concentrationThe combined organic layers were concentrated to dryness
  5. dissolutionThis residue was dissolved in dichloromethane (3 ml)
  6. stirringThe reaction mixture was stirred overnight at room temperature
  7. customThe reaction was quenched by addition of a saturated solution of sodium bicarbonate
  8. customAfter separating the layers
  9. extractionthe aqueous layer was extracted twice with ethyl acetate
  10. concentrationconcentrated under reduced pressure
  11. customyielding a white solid
  12. customThis solid was further purified by column chromatography
  13. customaffording two components as a white solid

Sources & evidence

ORD record
ord-5616932022db4986b24450b68a254823
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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