Ammonia → HCID 22341203, compound

HRID 584666Notes

Reaction equation

HRID 584666 reaction equation
[NH3:1].[Cl:2][C:3]1[C:4]([Cl:15])=[C:5]2[C:10](=C[CH:12]=1)[N:9]=[C:8](Cl)C(Cl)=N2.[Na+].[CH3:17][S:18]([O-:20])=[O:19].C[N:22]([CH:24]=O)[CH3:23]>>[Cl:2][C:3]1[CH:12]=[C:23]2[C:10](=[CH:5][C:4]=1[Cl:15])[N:9]=[C:8]([NH2:1])[C:24]([S:18]([CH3:17])(=[O:20])=[O:19])=[N:22]2

Participants

5

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 2733271Sodium methanesulfinateHCID 22341137HCID 22341137, compound

Product 1

HCID 22341203HCID 22341203, compound

Conditions

Temperature
0 °C

Procedure

Dry ammonia gas was bubbled through a solution of tetrachloroquinoxaline (260 mg, 0.97 mmol) in dry DMF (20 ml), while stirring at 0° C. After 20 minutes, the reaction was allowed to warm to room temperature and bubbling was continued for an additional 15 minutes. The reaction mixture was then concentrated to dryness in vacuo. To a suspension of the resulting 2,6,7-trichloro-3-aminoquinoxaline in DMF was added methanesulfinic acid sodium salt (230 mg, 2.2 mmol). The reaction was stirred overnight at room temperature. After removing the solvent in vacuo, the residue was taken up in ethyl acetate and water. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined and evaporated in vacuo. (6,7-Dichloro-3-methylsulfonylquinoxalin-2-yl)amine was purified by flash column chromatography using ethyl acetate:hexane 1:3 to obtain a yellow solid.

Workup

  1. temperatureto warm to room temperature
  2. custombubbling
  3. waitwas continued for an additional 15 minutes
  4. concentrationThe reaction mixture was then concentrated to dryness in vacuo
  5. additionTo a suspension of the resulting 2,6,7-trichloro-3-aminoquinoxaline in DMF
  6. stirringThe reaction was stirred overnight at room temperature
  7. customAfter removing the solvent in vacuo
  8. customThe layers were separated
  9. extractionthe aqueous layer was extracted twice with ethyl acetate
  10. customevaporated in vacuo
  11. custom(6,7-Dichloro-3-methylsulfonylquinoxalin-2-yl)amine was purified by flash column chromatography
  12. customto obtain a yellow solid

Sources & evidence

ORD record
ord-8bdbeca339ef4b44a6c7d0726ecbb7fc
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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