Potassium Carbonate → HCID 53812208, compound

HRID 343802Notes

Reaction equation

HRID 343802 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:3]=1[CH3:21].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[N:9]2)=[C:4]([N:16]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[S:17]([CH3:20])(=[O:19])=[O:18])[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 53906871HCID 53906871, compound

Product 1

HCID 53812208HCID 53812208, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)methanesulphonamide (694 mg, 2.09 mmol), potassium carbonate (347 mg, 2.51 mmol) and acetone (21 ml) was heated at reflux for 10 minutes and was then allowed to cool to room temperature. Methyl bromoacetate (396 μl, 640 mg, 4.19 mmol) was added and the mixture was heated at reflux for 18 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed twice with water and then brine and then dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with dichloromethane to give N-(7-chloro-2,3-dimethoxy-6-methylquinoxalin-5-yl)-N-(methoxycarbonylmethyl)methanesulphonamide as a white solid (407 mg, 48%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 minutes
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 18 hours
  5. temperatureto cool to room temperature
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in dichloromethane
  8. washwashed twice with water
  9. dry with materialbrine and then dried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-8ee385b7e848465ea69f248b08709d3b
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

Loading…