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

HRID 583482

반응식

HRID 583482 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 gf 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 g, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-5aad2cea920c49739b25da5c2dc544c4
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05929114

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