3-Bromoaniline → 2,2'-Dithiobis[N-(3-bromophenyl)benzamide]

HRID 3713

Reaction equation

HRID 3713 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].[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>ClCCl.N1C=CC=CC=1>[Br:21][C:22]1[CH:23]=[C:24]([NH:25][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:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:22]([Br:21])[CH:23]=2)=[O:13])[CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 115623-BromoanilineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 189353082,2'-Dithiobis[N-(3-bromophenyl)benzamide]Yield 55.8%

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-bromoaniline (1.98 g, 11.6 mmol) in 16 mL of pyridine. The crude product was recrystallized from ethyl acetate-hexanes to yield 1.99 g of the title compound, mp 194°-196° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was recrystallized from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-b72f28adf1044fce8dbba03ec99cbcd2
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

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