m-Toluidine → 2,2'-Dithiobis[N-(3-methylphenyl)benzamide]

HRID 583499

Reaction equation

HRID 583499 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]=[C:24]([CH3:28])[CH:23]=1>ClCCl.N1C=CC=CC=1>[CH3:28][C:24]1[CH:23]=[C:22]([NH:21][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:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)=[O:13])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 7934m-ToluidineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 4653262,2'-Dithiobis[N-(3-methylphenyl)benzamide]Yield 42%

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 m-toluidine (1.24 g, 11.6 mmol) in 10 mL of pyridine. The crude product was recrystallized from ethyl ether-ethyl acetate to yield 1.18 g of the title compound, mp 193-195° C.

Workup

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

Sources & evidence

ORD record
ord-fb8b0462d70a4d8bbb0a5ec5ccac4712
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Linked notes

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