Chloroacetonitrile → HCID 22097030, compound

HRID 1458561Notes

Reaction equation

HRID 1458561 reaction equation
Cl[CH2:2][C:3]#[N:4].[Cl:5][C:6]1[C:7]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:5][C:6]1[C:7]([N:21]([CH2:2][C:3]#[N:4])[S:22]([CH3:25])(=[O:24])=[O:23])=[C:8]2[C:13](=[CH:14][C:15]=1[Cl:16])[N:12]=[C:11]([O:17][CH3:18])[C:10]([O:19][CH3:20])=[N:9]2

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 54321377HCID 54321377, compound

Product 1

HCID 22097030HCID 22097030, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Chloroacetonitrile (233 μl, 279 mg, 3,69 mmol) was added to a refluxing mixture of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)methane-sulphonamide (from Preparation 3, 1.00 g, 2.84 mmol) and potassium carbonate (0.47 g, 3.41 mmol) in acetone (50 ml) under nitrogen. The mixture was refluxed for 18 h and was then allowed to cool, and was partitioned between ethyl acetate (500 ml) and water (500 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 0-100% ethyl acetate in hexane and then 5% methanol in dichloromethane) to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(cyanomethyl) methanesulphonamide as an off-white solid (600 mg, 54%).

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperatureto cool
  3. customwas partitioned between ethyl acetate (500 ml) and water (500 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (
  7. washeluting with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-14f6b7edb2cc4a298d26aa83bd8b6c29
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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