Diethyl Ether → 5-(4-Methoxy-benzoyl)-2-methyl-benzenesulfonamide

HRID 873629Notes

Reaction equation

HRID 873629 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[S:15](=[O:18])(=[O:17])[NH2:16].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OCC)C>C(Cl)Cl.C(OCC)(=O)C>[CH3:26][O:25][C:19]1[CH:24]=[CH:23][C:22]([C:10]([C:9]2[CH:13]=[CH:14][C:6]([CH3:5])=[C:7]([S:15]([NH2:16])(=[O:18])=[O:17])[CH:8]=2)=[O:11])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 227605604-Methyl-3-sulfamoyl-benzoyl chloride

Product 1

HCID 581074525-(4-Methoxy-benzoyl)-2-methyl-benzenesulfonamideYield 58.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of aluminium chloride (906 mg, 6.8 mmol) in methylene chloride (20 mL) is added 4-methyl-3-sulfamoyl-benzoyl chloride (1.1 g, 4.7 mmol) and anisole (1.1 g, 10.2 mmol). After the mixture is stirred at room temperature for 16 h, the reaction is quenched with 6 N HCl, and extracted with methylene chloride three times. The combined organic layers are washed with a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. On standing, crystals form and trituration with diethyl ether and ethyl acetate provides 0.84 g (58% yield) of the title compound as a white solid. MS (m/z): 306 (M+1).

Workup

  1. customthe reaction is quenched with 6 N HCl
  2. extractionextracted with methylene chloride three times
  3. washThe combined organic layers are washed with a saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f04e14f40dd48cfb3732e2d6bcfde5d
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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