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

HRID 3695

Reaction equation

HRID 3695 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 465369N-[(4-sulfamoylphenyl)methyl]-2-[[2-[(4-sulfamoylphenyl)methylcarbamoyl]phenyl]disulfanyl]benzamideYield 35.4%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-71cd525c3da84d9d811cf5b361bea38c
Source dataset
uspto-grants-1998_03
Patent number
US05734081

Linked notes

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