Tetrahydrofuran → HCID 53820193, compound

HRID 343814Notes

Reaction equation

HRID 343814 reaction equation
[C:1]([CH2:4][N:5]([C:10]1[C:19]([Cl:20])=[C:18]([Cl:21])[CH:17]=[C:16]2[C:11]=1[N:12]=[C:13]([O:24][CH3:25])[C:14](OC)=[N:15]2)[S:6]([CH3:9])(=[O:8])=[O:7])(O)=[O:2].[OH2:26].[NH2:27][NH2:28].O1CCC[CH2:30]1>>[Cl:20][C:19]1[C:10]([N:5]([CH2:4][C:1]([NH:27][NH2:28])=[O:2])[S:6]([CH3:9])(=[O:8])=[O:7])=[C:11]2[C:16](=[CH:17][C:18]=1[Cl:21])[N:15]=[C:14]([O:26][CH3:30])[C:13]([O:24][CH3:25])=[N:12]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 54166571HCID 54166571, compound

Product 1

HCID 53820193HCID 53820193, compoundYield 29%

Procedure

A mixture of N-(carboxymethyl)-N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)methanesulphonamide (500 mg, 1.219 mmol) and N,N'-carbonyldiimidazole (296 mg, 1.828 mmol) in dry tetrahydrofuran (15 ml) was heated at reflux for 1 hour, cooled and concentrated under reduced pressure. The residue was partitioned between dichloromethane (20 ml) and water (10 ml). The organic solution was dried (MgSO4) and concentrated under reduced pressure. The residue was dissolved in dry tetrahydrofuran and hydrazine hydrate (122 mg, 2.438 mmol) added. After stirring at room temperature for 3 hours, the solvent was removed under reduced pressure and the residue partitioned between dichloromethane (20 ml) and saturated brine (10 ml). The aqueous layer was extracted with dichloromethane (20 ml) and the combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel, eluting with dichloromethane:methanol 98:2, gave N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(hydrazinocarbonylmethyl)methanesulphonamide (150 mg, 29%) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between dichloromethane (20 ml) and water (10 ml)
  6. dry with materialThe organic solution was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. dissolutionThe residue was dissolved in dry tetrahydrofuran
  9. customthe solvent was removed under reduced pressure
  10. customthe residue partitioned between dichloromethane (20 ml) and saturated brine (10 ml)
  11. extractionThe aqueous layer was extracted with dichloromethane (20 ml)
  12. dry with materialthe combined organic solutions were dried (MgSO4)
  13. concentrationconcentrated under reduced pressure
  14. customPurification by flash chromatography on silica gel
  15. washeluting with dichloromethane:methanol 98:2

Sources & evidence

ORD record
ord-224029d29cdd482aa754a1fd893309be
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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