P-Toluenesulfonamide → N-(3-Chloroquinoxalin-2-yl)-4-methylbenzene-1-sulfonamide

HRID 1186311Notes

Reaction equation

HRID 1186311 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.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:12][C:11]1[C:2]([NH:23][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)(=[O:21])=[O:22])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 11430Potassium CarbonateHCID 166592,3-Dichloroquinoxaline

Product 1

HCID 677919N-(3-Chloroquinoxalin-2-yl)-4-methylbenzene-1-sulfonamideYield 74%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

According to the step of Example 6-1, by use of 2,3-dichloroquinoxaline (1.00 g, 5.02 mmol) dissolved in dimethyl sulfoxide (30 mL), 4-methylbenzene-1-sulfonamide (860 mg, 5.02 mmol) and potassium carbonate (694 mg, 5.02 mmol), the mixture was stirred and reacted at 150° C. for 4.2 hours. Then, slurry purification was performed using diisopropyl ether, to give N-(3-chloroquinoxalin-2-yl)-4-methylbenzenesulfonamide (Compound AB) (1.24 g, yield: 74%).

Workup

  1. customreacted at 150° C. for 4.2 hours
  2. customThen, slurry purification

Sources & evidence

ORD record
ord-97289a7a9d81467195b9963d26ece79b
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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