Hydrochloric Acid → N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide

HRID 237362

Reaction equation

HRID 237362 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.[N+:13]([C:16]1[CH:17]=[C:18]([S:22]([NH2:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.O>[Cl:12][C:11]1[C:2]([NH:25][S:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([N+:13]([O-:15])=[O:14])[CH:17]=2)(=[O:24])=[O:23])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 67138Benzenesulfonamide, 3-nitro-

Product 1

HCID 5007601N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

2,3-Dichloroquinoxaline (26.1 g, 131.1 mmol), m-Nitrobenzene sulfonamide (26.5 g, 131.1 mmol) and potassium carbonate (18.1 g, 131.1) were dissolved in anhydrous DMSO (500 mL). The reaction was heated to 150° C. for 2 h. The reaction mixture was poured into water (400 mL), followed by addition of 2M HCl (60 mL). The product was extracted with EtOAc (3×500 mL). The organic layers were combined and washed water (2×500 mL) and brine (2×500 mL). The product was then dried with sodium sulfate to give N-(3-chloroquinoxalin-2-yl)-3-nitrobenzenesulfonamide. MS (EI) for C14H9ClN4O4S: 364.94, 366.97 (MH+)

Workup

  1. extractionThe product was extracted with EtOAc (3×500 mL)
  2. washwashed water (2×500 mL) and brine (2×500 mL)
  3. dry with materialThe product was then dried with sodium sulfate

Sources & evidence

ORD record
ord-c2d2f7f0d90d43d5b762d39a4c2ce1a8
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Linked notes

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