Acetic Acid → 2,3-dichloro-N-{3-chloroquinoxalin-2-yl}benzenesulfonamide

HRID 1186310Notes

Reaction equation

HRID 1186310 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[S:21]([NH2:24])(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>CS(C)=O>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[S:21]([NH:24][C:2]1[C:11]([Cl:12])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)(=[O:22])=[O:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 83179472,3-Dichlorobenzenesulfonamide

Product 1

HCID 866579282,3-dichloro-N-{3-chloroquinoxalin-2-yl}benzenesulfonamideYield 78.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

2,3-Dichloroquinoxaline (1.00 g, 5.02 mmol), 2,3-dichlorobenzenesulfonamide (1.41 g, 5.02 mmol) and potassium carbonate (694 mg, 5.02 mmol) were suspended in dimethyl sulfoxide (30 mL) and the mixture was stirred at 150° C. for 3 hours. The reaction mixture was slowly added to a mixture (300 ml) of a 1% aqueous acetic acid solution and ice, and the mixture was stirred for 3 hours. The resulting solid was collected by filtration and washed with water. Then, slurry purification was performed using diisopropyl ether, to give 2,3-dichloro-N-{3-chloroquinoxalin-2-yl}benzenesulfonamide (Compound AA) (1.53 g, yield: 78%).

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customThen, slurry purification

Sources & evidence

ORD record
ord-0ee91c783d064b49b046d9c432bcd921
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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