4-Aminobenzonitrile → Benzamide, 2,2'-dithiobis[N-(4-cyanophenyl)-

HRID 583512

Reaction equation

HRID 583512 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:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>ClCCl.N1C=CC=CC=1>[C:26]([C:25]1[CH:28]=[CH:29][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:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[O:13])=[CH:23][CH:24]=1)#[N:27]

Participants

5

Reactant 2

HCID 133964-AminobenzonitrileHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 465336Benzamide, 2,2'-dithiobis[N-(4-cyanophenyl)-Yield 12.5%

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 4-aminobenzonitrile (1.38 g, 11.7 mmol) in 11 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate and ethanol (1:1), filtered, and recrystallized from ethanol-DMF-water to yield 0.37 g of the title compound, mp 239-241° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was triturated with a hot mixture of ethyl acetate and ethanol (1:1)
  3. filtrationfiltered
  4. customrecrystallized from ethanol-DMF-water

Sources & evidence

ORD record
ord-c882ba6eee4a4d68a8874a5d94821c8d
Source dataset
uspto-grants-1999_07
Patent number
US05929114

Linked notes

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