3-Nitroaniline → 2,2'-Dithiobis(N-(3-nitrophenyl)benzamide)

HRID 583519

Reaction equation

HRID 583519 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].[N+:21]([C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27])([O-:23])=[O:22]>ClCCl.N1C=CC=CC=1>[N+:21]([C:24]1[CH:25]=[C:26]([NH:27][C:1](=[O:19])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][S:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:27][C:26]2[CH:28]=[CH:29][CH:30]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)=[O:13])[CH:28]=[CH:29][CH:30]=1)([O-:23])=[O:22]

Participants

5

Reactant 2

HCID 74233-NitroanilineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 4574682,2'-Dithiobis(N-(3-nitrophenyl)benzamide)Yield 24.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

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 3-nitroaniline (1.60 g, 11.6 mmol) in 13 mL of pyridine. The crude product was recrystallized once from ethanol-ether, then twice from acetonitrile-DMF-water to yield 0.79 g of the title compound, mp >270° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized once from ethanol-ether

Sources & evidence

ORD record
ord-c4137c4794924c2ea3db3cbf20e921ae
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Linked notes

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