Sulfacetamide → Benzamide, 2,2'-dithiobis(N-(4-((acetylamino)sulfonyl)phenyl)-

HRID 611637

Reaction equation

HRID 611637 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].[C:21]([NH:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26])(=[O:23])[CH3:22]>ClCCl.N1C=CC=CC=1>[C:21]([NH:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([NH:32][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:32][C:31]2[CH:33]=[CH:34][C:28]([S:25]([NH:24][C:21](=[O:23])[CH3:22])(=[O:27])=[O:26])=[CH:29][CH:30]=2)=[O:13])=[CH:30][CH:29]=1)(=[O:27])=[O:26])(=[O:23])[CH3:22]

Participants

5

Reactant 2

HCID 5320SulfacetamideHCID 881642,2'-Dithiodibenzoyl chloride

Product 1

HCID 462932Benzamide, 2,2'-dithiobis(N-(4-((acetylamino)sulfonyl)phenyl)-Yield 8.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

The compound was prepared according to the general method of Preparation 9 using 2,2'-dithiobisbenzoyl chloride (3.0 g, 8.0 mmol) in 30 mL of dichloromethane and 4-[(acetylamino)sulfonyl]aniline (5.6 g, 26.0 mmol) in 100 mL of pyridine. The crude product was purified on a silica gel column using chloroform/methanol (1:1 v/v) as the mobile phase. The pure fractions were pooled, concentrated in vacuo, and the solid was crystallized from ethanol/water (1:1 v/v) to yield 0.5 g of the title compound, mp 180-182° C.

Workup

  1. customThe compound was prepared
  2. customThe crude product was purified on a silica gel column
  3. concentrationconcentrated in vacuo
  4. customthe solid was crystallized from ethanol/water (1:1 v/v)

Sources & evidence

ORD record
ord-b7269c87172147c79e949fbbe99934c0
Source dataset
uspto-grants-1999_12
Patent number
US06001863

Linked notes

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