Water → HCID 53946910, compound

HRID 343816Notes

Reaction equation

HRID 343816 reaction equation
[Cl:1][C:2]1[C:3]([N:17]([CH2:22][CH2:23][CH2:24][OH:25])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:27].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.O>CN(C=O)C>[C:24]([CH2:23][CH2:22][N:17]([C:3]1[C:2]([Cl:1])=[C:11]([CH3:12])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:15][CH3:16])[C:7]([O:13][CH3:14])=[N:8]2)[S:18]([CH3:21])(=[O:20])=[O:19])([OH:27])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 2724130Cornforth reagentHCID 54567779HCID 54567779, compound

Product 1

HCID 53946910HCID 53946910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(6-Chloro-7-methyl-2,3-dimethoxyquinoxalin-5-yl)-N-(3-hydroxypropyl)methanesulphonamide (0.94 g, 2.41 mmol) and pyridinium dichromate (2.42 g, 9.63 mmol) in DMF (24 ml) were stirred at room temperature for 18 hours. The reaction mixture was poured into water (25 ml) and extracted twice with dichloromethane. The combined dichloromethane extracts were extracted twice with 10% potassium carbonate solution. The potassium carbonate extracts were acidified to pH1 with 2M HCl and extracted twice with dichloromethane. These combined dichloromethane extracts were dried (MgSO4) and concentrated under reduced pressure to give N-(2-carboxyethyl)-N-(6-chloro-7-methyl-2,3-dimethoxyquinoxalin-5-yl)methanesulphonamide an off-white solid (0.49 g, 51%).

Workup

  1. extractionextracted twice with dichloromethane
  2. extractionThe combined dichloromethane extracts were extracted twice with 10% potassium carbonate solution
  3. extractionextracted twice with dichloromethane
  4. dry with materialThese combined dichloromethane extracts were dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d12a0de0ae35476fbd49f20b520330e1
Source dataset
uspto-grants-1999_01
Patent number
US05863917

Reaction notes

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