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Melatonin → n-{2-[5-Methoxy-1-(phenylsulphonyl)-1h-indol-3-yl]ethyl}acetamide

HRID 382324
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반응식

HRID 382324 반응식
[CH3:1][C:2]([NH:4][CH2:5][CH2:6][C:7]1[C:11]2[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=2[NH:9][CH:8]=1)=[O:3].[OH-].[Na+].[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][O:16][C:13]1[CH:12]=[C:11]2[C:10](=[CH:15][CH:14]=1)[N:9]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:8]=[C:7]2[CH2:6][CH2:5][NH:4][C:2](=[O:3])[CH3:1]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 896MelatoninHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

생성물 1

HCID 11090036n-{2-[5-Methoxy-1-(phenylsulphonyl)-1h-indol-3-yl]ethyl}acetamide

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane
용매

실험 절차

5 g of melatonin are dissolved in 150 ml of dichloromethane, and then 3.41 g of sodium hydroxide and 0.35 g of tetrabutylammonium hydrogen sulphate are added. The reaction mixture is then cooled in an ice-bath, and 4.06 ml of benzenesulphonyl chloride are added dropwise. After stirring overnight at room temperature, the excess sodium hydroxide and the catalyst are filtered off, the solvent is removed by evaporation in vacuo, and the resulting solid is recrystallised to yield the title product in the form of white crystals.

후처리

  1. temperatureThe reaction mixture is then cooled in an ice-bath
  2. filtrationthe excess sodium hydroxide and the catalyst are filtered off
  3. customthe solvent is removed by evaporation in vacuo
  4. customthe resulting solid is recrystallised

출처 및 근거

ORD 기록
ord-772d898a01774a5f803c6fe47044ad3a
출처 데이터셋
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06310074B1

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