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

HRID 3695
ノート
印刷プレビュー

反応式

HRID 3695 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine
溶媒
HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-71cd525c3da84d9d811cf5b361bea38c
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05734081

反応ノート

読み込み中…

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