Pyridine → 3-chloro-2-methyl-N-(3-methyl-benzo[d]isoxazol-5-yl)-benzenesulfonamide

HRID 1766302Notes

Reaction equation

HRID 1766302 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]=[CH:22][C:23]2[O:27][N:26]=[C:25]([CH3:28])[C:24]=2[CH:29]=1.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]=[CH:22][C:23]3[O:27][N:26]=[C:25]([CH3:28])[C:24]=3[CH:29]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 213453975-Amino-3-methylbenzo[d]isoxazole

Product 1

HCID 112676953-chloro-2-methyl-N-(3-methyl-benzo[d]isoxazol-5-yl)-benzenesulfonamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (128 mg, 0.567 mmol) in dichloromethane (3 mL) was added pyridine (110 μL, 1.35 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-1,2-benzisoxazole [26] (80 mg, 0.54 mmol) was added. The resulting mixture was stirred for 4 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 a white solid (88 mg, 48%), single spot at Rf 0.58 (1:1 hexane:ethyl acetate). mp 162.8-163.2° C., HPLC purity 99+% (tR 2.26 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.80 (1H, dd, J=7.9, 1.3 Hz), 7.55 (1H, dd, J=8.1, 1.1 Hz), 7.38 (2H, m), 7.17 (1H, t, J=8.1 Hz), 7.10 (1H, dd, J=8.8, 2.2 Hz), 6.72 (1H, s, N−H), 2.72 (3H, s), 2.50 (3H, s). LCMS: 320.00 (M−CH3). FAB-MS (MH+, C15H13ClN2O3S): calcd 337.0413, found 337.0422.

Workup

  1. stirringThe resulting mixture was stirred for 4 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-526e880e6cc0491aa86b4a4cfe605aaf
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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