4-Methoxybenzenesulfonyl chloride → HCID 54048961, compound

HRID 583303Notes

Reaction equation

HRID 583303 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[NH2:11].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[C:5]=1[NH:11][S:21]([C:18]1[CH:17]=[CH:16][C:15]([O:14][CH3:13])=[CH:20][CH:19]=1)(=[O:23])=[O:22]

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 205248Anthranilic acid, 3-hydroxy-, methyl ester

Product 1

HCID 54048961HCID 54048961, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 0.748 g (4.48 mmol) of the product of Example 30 in 10.0 mL of pyridine was added 0.928 g (4.48 mmol) of p-methoxybenzenesulfonyl chloride. The reaction mixture was stirred for 24 h at room temperature and then diluted with chloroform and washed with 5% HCl solution and water. The organic layer was then dried over MgSO4, filtered and concentrated in vacuo. The residue was triturated with ether-hexanes and the resulting solid was filtered and dried to provide 0.86 g (57%) of the desired product as a tan solid. Electrospray Mass Spec: 338.2 (M+H)+

Workup

  1. washwashed with 5% HCl solution and water
  2. dry with materialThe organic layer was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with ether-hexanes
  6. filtrationthe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-1c97368a6e494b4c81abe32d5d03d322
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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