Hydrochloric Acid → HCID 698553, compound

HRID 336805Notes

Reaction equation

HRID 336805 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.[C:13]1([S:19]([NH2:22])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>ClCCl.C(OCC)(=O)C.O.CS(C)=O>[Cl:12][C:11]1[C:2]([NH:22][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7370BenzenesulfonamideHCID 10796Cesium carbonateHCID 166592,3-Dichloroquinoxaline

Product 1

HCID 698553HCID 698553, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A flask was charged with 2,3-dichloroquinoxaline (3.5 g, 18 mmol), 85 mL of dimethylsulfoxide, benzene sulfonamide (2.8 g, 18 mmol), and cesium carbonate (5.8 g, 18 mmol). The reaction mixture was stirred under an N2 atmosphere for 15 h at 150° C., after which time, it was transferred to a separatory funnel and 100 mL of water were added. Concentrated HCl was then added in order to acidify the reaction mixture to pH<2. The aqueous layer was subsequently washed three times with 90 mL ethyl acetate. The ethyl acetate layers were then washed two times with 150 mL water, three times with 100 mL brine and then dried over sodium sulfate. The ethyl acetate was removed on a rotary-evaporator. A slurry was formed by adding ethyl acetate and dichloromethane to the dried crude product, filtration yielded N-(3-chloroquinoxalin-2-yl)-benzenesulfonamide which was used without further purification. MS (EI) m/z C14H10ClN3O2S: 319.9 (MH+).

Workup

  1. customafter which time, it was transferred to a separatory funnel
  2. washThe aqueous layer was subsequently washed three times with 90 mL ethyl acetate
  3. washThe ethyl acetate layers were then washed two times with 150 mL water, three times with 100 mL brine
  4. dry with materialdried over sodium sulfate
  5. customThe ethyl acetate was removed on a rotary-evaporator
  6. customA slurry was formed
  7. customdried
  8. filtrationcrude product, filtration

Sources & evidence

ORD record
ord-7e4cdf002ac64c749b6dac786c45f38c
Source dataset
uspto-grants-2014_11
Patent number
US08889664B2

Reaction notes

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