Pyridine → 3-chloro-N-(2.3-dimethyl-quinoxalin-6-yl)-2-methyl-benzenesulfonamide

HRID 1766295Notes

Reaction equation

HRID 1766295 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([CH3:30])[C:24]([CH3:31])=[N:23]2.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[C:25]([CH3:30])[C:24]([CH3:31])=[N:23]3)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 1460536-Quinoxalinamine, 2,3-dimethyl-HCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chloride

Product 1

HCID 113373913-chloro-N-(2.3-dimethyl-quinoxalin-6-yl)-2-methyl-benzenesulfonamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (109 mg, 0.485 mmol) in dichloromethane (3 mL) was added pyridine (90 μL, 1.2 mmol) and the mixture was stirred under N2 for 5 min, after which time 6-amino-2,3-dimethylquinoxaline [22] (80 mg, 0.46 mmol) was added. The resulting mixture was stirred for 6 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford an off-white solid (152 mg, 91%), single spot at Rf 0.70 (ethyl acetate). mp 225.3-225.7° C. HPLC purity 99+% (tR 2.29 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.99 (1H, d, 4=7.9. Hz), 7.85 (1H, d, J=9.2 Hz), 7.54-7.52 (2H, m), 7.40 (1H, dd, J=9.1, 2.6 Hz), 7.21 (1H, t, J=7.9 Hz), 6.95 (1H, s, N—H, 2.75 (3H, s), 2.67 (6H, s). LCMS: 360.24 (M−). FAB-MS (MH+, C17H16ClN3O2S): calcd 362.0730, found 362.0732.

Workup

  1. stirringThe resulting mixture was stirred for 6 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-12aa8c8a18e646dbbe0c13c2d4381031
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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