2-Aminobenzenesulfonamide → N-(2-sulfamoylphenyl)-2-[[2-[(2-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]benzamide

HRID 3732

Reaction equation

HRID 3732 reaction equation
[C:1](Cl)(=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH2:31])(=[O:30])=[O:29]>ClCCl.N1C=CC=CC=1>[NH2:31][S:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[NH:21][C:1](=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][S:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28]([NH2:31])(=[O:29])=[O:30])=[O:13])(=[O:29])=[O:30]

Participants

5

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 462931N-(2-sulfamoylphenyl)-2-[[2-[(2-sulfamoylphenyl)carbamoyl]phenyl]disulfanyl]benzamideYield 19.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

This compound was prepared according to the general method of Example 77 using 2,2'-dithiobisbenzoyl chloride (2.00 g, 5.83 mmol) in 50 mL of dichloromethane and 2-aminobenzenesulfonamide (2.00 g, 11.6 mmol) in 16 mL of pyridine. The reaction mixture was stirred for 6 days at 23° C. under nitrogen atmosphere. The crude product was recrystallized from acetonitrile to yield 0.70 g of the title compound, mp 150°-151° C. (dec.).

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-8758a287794b4b4db01fbda93c571355
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

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