2-Methylbenzenesulfonamide → N-[1-(3-nitrobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide

HRID 2081699

반응식

HRID 2081699 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O-:3])=[O:2].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH2:33])(=[O:32])=[O:31].Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([NH:33][S:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH3:23])(=[O:31])=[O:32])=[O:19])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197804001-(3-Nitrobenzyl)indole-5-carboxylic acid

생성물 1

HCID 19780401N-[1-(3-nitrobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

The carboxylic acid (Example 2) (6.2 g) was stirred at room temperature in dichloromethane (50 ml) with 2-methylbenzene sulphonamide (3.4 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.6 g) and 4-dimethylaminopyridine (0.25 g) for 72 hours. The reaction mixture was diluted with dichloromethane and washed with 0.5N hydrochloric acid, then water. The organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with 0-2% ethyl acetate in dichloromethane, afforded N-[1-(3-nitrobenzyl)indol-5-ylcarbonyl]-2-methylbenzene sulphonamide (m.p. 208°-210° C.).

후처리

  1. washwashed with 0.5N hydrochloric acid
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customPurification by flash chromatography on silica
  7. washeluting with 0-2% ethyl acetate in dichloromethane

출처 및 근거

ORD 기록
ord-8df1e7b3eceb4c2f97c3218778cb9624
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05185361

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