4-Aminobenzamide → HCID 465343, compound

HRID 1378824Notes

Reaction equation

HRID 1378824 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:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=1>ClCCl.N1C=CC=CC=1>[NH2:28][C:26]([C:25]1[CH:29]=[CH:30][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:30]=[CH:29][C:25]([C:26]([NH2:28])=[O:27])=[CH:24][CH:23]=2)=[O:13])=[CH:23][CH:24]=1)=[O:27]

Participants

5

Reactant 2

HCID 760794-AminobenzamideHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 465343HCID 465343, compoundYield 8.9%

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 (4.00 g, 11.7 mmol) in 100 mL of dichloromethane and 4-aminobenzamide (3.20 g, 23.5 mmol) in 26 mL of pyridine. The crude product was triturated with a hot mixture of acetonitrile and DMF, filtered, recrystallized from ethanol-water-DMF, triturated with a hot mixture of methanol and DMF, and filtered to yield 0.563 g of the title compound, mp >270° C.

Workup

  1. customThis compound was prepared
  2. customThe crude product was triturated with a hot mixture of acetonitrile and DMF
  3. filtrationfiltered
  4. customrecrystallized from ethanol-water-DMF
  5. customtriturated with a hot mixture of methanol and DMF
  6. filtrationfiltered

Sources & evidence

ORD record
ord-e6b04ec3c82b43b1a2a1f49143dabe56
Source dataset
uspto-grants-1997_09
Patent number
US05668291

Reaction notes

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