Benzenesulfonyl chloride → N-(2-methoxyphenyl)-2-(4-nitrophenylthio)-6-(phenylsulfonamido)benzamide

HRID 1476708

Reaction equation

HRID 1476708 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH3:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH:6][C:4](=[O:5])[C:3]1[C:2]([NH:1][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])=[CH:18][CH:17]=[CH:16][C:15]=1[S:19][C:20]1[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 718115872-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl-thio)benzamide

Product 1

HCID 118402644N-(2-methoxyphenyl)-2-(4-nitrophenylthio)-6-(phenylsulfonamido)benzamideYield 67%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 25 (1.0 equiv.) was dissolved in azabenzene (40 mL) at room temperature. To this mixture was added benzenesulfonyl chloride (1.2 equiv.). After being stirred for 10 Hours at room temperature, the reaction mixture was concentrated under reduced pressure. The crude residue was diluted ethyl acetate (50 mL), washed with water (3×20 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a white solid. 67% yield;

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. washwashed with water (3×20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)
  7. customto provide a white solid

Sources & evidence

ORD record
ord-6f8ebbac375646b1b282f1ad582046b0
Source dataset
uspto-grants-2016_08
Patent number
US09402819B2

Linked notes

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