2,4-Dichloroaniline → N-(2,4-dichlorophenyl)-2-[[2-[(2,4-dichlorophenyl)carbamoyl]phenyl]disulfanyl]benzamide

HRID 3716

Reaction equation

HRID 3716 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].[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH2:24]>ClCCl.N1C=CC=CC=1>[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH:24][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:24][C:23]1[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:22]=1[Cl:21])=[O:13]

Participants

5

Reactant 2

HCID 111232,4-DichloroanilineHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 6483556N-(2,4-dichlorophenyl)-2-[[2-[(2,4-dichlorophenyl)carbamoyl]phenyl]disulfanyl]benzamideYield 18.5%

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 2,4-dichloroaniline (1.89 g, 11.7 mmol) in 15 mL of pyridine. The crude product was triturated with a hot mixture of ethyl acetate, ethanol and methanol (1:1:1) and filtered to yield 0.64 g of the title compound, mp 227°-228° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was triturated with a hot mixture of ethyl acetate, ethanol and methanol (1:1:1)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a52bb8c1753c453fa00de43f77a5ce8a
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

Loading…