Iodoethane → HCID 22097014, compound

HRID 1458557Notes

Reaction equation

HRID 1458557 reaction equation
[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:8]([Cl:17])=[C:7]([C:18]([F:21])([F:20])[F:19])[CH:6]=2.C(=O)([O-])[O-].[K+].[K+].I[CH2:31][CH3:32]>CC(C)=O>[NH2:1][C:2]1[C:3]([O:22][CH3:23])=[N:4][C:5]2[C:10]([N:11]=1)=[C:9]([N:12]([CH2:31][CH3:32])[S:13]([CH3:16])(=[O:15])=[O:14])[C:8]([Cl:17])=[C:7]([C:18]([F:21])([F:20])[F:19])[CH:6]=2

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 11430Potassium CarbonateHCID 22097003HCID 22097003, compound

Product 1

HCID 22097014HCID 22097014, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(3-amino-6-chloro-7-trifluoromethyl-2-methoxyquinoxalin-5-yl)methanesulphonamide (Preparation 20, 73 mg, 0.2 mmol) and anhydrous potassium carbonate (33 mg, 0.24 mmol) in acetone was stirred under reflux for 20 mins. Iodoethane (32 μl, 0.4 mmol) was added, and the mixture was heated for a further 2 h. Additional iodoethane (32 μl, 0.4 mmol) was added, and heating was continued for a further 4 h. The mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic solution was dried (MgSO4), concentrated under reduced pressure, and the residue was purified by flash chromatography (gradient elution with dichloromethane/methanol) to give N-(3-amino-6-chloro-7-trifluoromethyl-2-methoxyquinoxalin-5-yl)-N-ethyl-methanesulphonamide (75 mg, 96%), as a white solid.

Workup

  1. temperatureunder reflux for 20 mins
  2. temperaturethe mixture was heated for a further 2 h
  3. temperatureheating
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue was partitioned between water and ethyl acetate
  6. dry with materialThe organic solution was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by flash chromatography (gradient elution with dichloromethane/methanol)

Sources & evidence

ORD record
ord-2c9cd9cd962443f99d0ef8bfb5f389e4
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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