4-Methoxybenzenesulfonyl chloride → 5-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl ester

HRID 583335Notes

Reaction equation

HRID 583335 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH2:12].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[NH:12][S:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][CH3:14])=[CH:21][CH:20]=1)(=[O:24])=[O:23]

Participants

3

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 2763413Methyl 2-amino-5-bromo-3-methylbenzoate

Product 1

HCID 542183595-Bromo-2-(4-methoxy-benzenesulfonylamino)-3-methyl-benzoic acid methyl esterYield 84.5%

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 24.5 g (100 mmol) of the product of Example 133 in 100 mL of pyrdine was added 21.0 g (100 mmol) of p-methoxybenzenesulfonyl chloride and the resulting mixture was heated to 80° C. for 24 h. The reaction mixture was then quenched with ice cold water and acidified with concentrated HCl. The resulting mixture was extracted with chloroform, washed with water, dried over MgSO4, filtered and concentrated in vacuo. The residue was triteretd with diethyl ether, filtered and dried to provide 35 g (84%) of the desired product as a brown solid. Electrospray Mass Spec 416, (M+H).

Workup

  1. customThe reaction mixture was then quenched with ice cold water
  2. extractionThe resulting mixture was extracted with chloroform
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-099e291be6ed479c86d95d408f284ad9
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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