N-Trimethylsilyl-N-methylacetamide → N-[(4-sulfamoylphenyl)methyl]-2-[[2-[(4-sulfamoylphenyl)methylcarbamoyl]phenyl]disulfanyl]benzamide

HRID 3695

Reaktionsgleichung

Reaktionsgleichung von HRID 3695
[OH2:1].Cl.[NH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:13])=[O:12])=[CH:7][CH:6]=1.C[N:16]([Si](C)(C)C)[C:17](=O)[CH3:18].[C:24](Cl)(=[O:42])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[S:31][S:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35](Cl)=[O:36]>N1C=CC=CC=1.ClCCl>[NH2:14][S:11]([C:8]1[CH:7]=[CH:6][C:5]([CH2:4][NH:3][C:24](=[O:42])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[S:31][S:32][C:33]2[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=2[C:35]([NH:16][CH2:17][C:18]2[CH:10]=[CH:9][C:8]([S:11]([NH2:14])(=[O:12])=[O:1])=[CH:7][CH:6]=2)=[O:36])=[CH:10][CH:9]=1)(=[O:12])=[O:13]

Komponenten

6

Edukt 3

HCID 81953N-Trimethylsilyl-N-methylacetamideHCID 881642,2'-Dithiodibenzoyl chlorideHCID 215845674-(Aminomethyl)benzenesulfonamide hydrochloride hydrate

Produkt 1

HCID 465369N-[(4-sulfamoylphenyl)methyl]-2-[[2-[(4-sulfamoylphenyl)methylcarbamoyl]phenyl]disulfanyl]benzamideAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 g, 29 mmol) in 100 mL pyridine was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (13.4 mL, 83.0 mmol) until a homogenous solution occurred. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobisbenzoyl chloride (4.0 9, 16.0 mmol) in 20 mL dichloromethane was added dropwise. The resulting solution was allowed to stir for 18 hours and the dichloromethane was removed in vacuo. The crude product was precipitated with the addition of water and the resulting solid was collected by filtration. The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water to yield 3.3 g of the title compound, mp 267°-269° C.

Aufarbeitung

  1. temperatureThe solution was cooled to 0° C. to 5° C.
  2. customthe dichloromethane was removed in vacuo
  3. customThe crude product was precipitated with the addition of water
  4. filtrationthe resulting solid was collected by filtration
  5. customThe crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water

Quellen und Nachweise

ORD-Eintrag
ord-71cd525c3da84d9d811cf5b361bea38c
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05734081

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