Dimethyl Sulfoxide → HCID 57448734, compound

HRID 237353Notes

Reaction equation

HRID 237353 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[N: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>CC(O)=O>[Cl:13][C:14]1[N:19]=[CH:18][C:17]([S:20]([NH:23][C:2]2[C:11]([Cl:12])=[N:10][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)(=[O:21])=[O:22])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 12015126-chloropyridine-3-sulfonamide

Product 1

HCID 57448734HCID 57448734, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,3-dichloroquinoxaline (1.09 g, 5.48 mmol), 6-chloropyridine-3-sulfonamide (1.05 g, 5.45 mmol), K2CO3 (753 mg, 5.45 mmol) and dry DMSO (30 mL) were combined and heated to 150 C with vigorous stirring for 3-4 hr. The reaction mixture was allowed to cool to room temperature, then poured into 1% AcOH in ice water (300 mL) with vigorous stirring. The resulting solids were filtered, washed with H2O and dried under high vacuum to give 6-chloro-N-(3-chloroquinoxalin-2-yl)pyridine-3-sulfonamide (1.87 g, 96%). MS (EI) for C13H8Cl2N4O2S: 354.99 (MH+).

Workup

  1. temperatureheated to 150 C
  2. filtrationThe resulting solids were filtered
  3. washwashed with H2O
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7be0a4ff8ea340628d688756b162b602
Source dataset
uspto-grants-2014_02
Patent number
US08642584B2

Reaction notes

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