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

HRID 429776
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반응식

HRID 429776 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

Dissolve 5 g (21.5 mmol) of melatonin in 150 ml of dichloromethane. With stirring, add 3.41 g (84 mmol) of sodium hydroxide and 0.35 g (0.9 mmol) of tetrabutylammonium hydrogen sulphate. Cool the mixture in an ice-bath, and add 4.06 ml (31.5 mmol) of benzenesulphonyl chloride dropwise. After stirring overnight at room temperature, filter off the excess sodium hydroxide and the catalyst. Remove the solvent by evaporation in vacuo, and recrystallise the resulting solid.

후처리

  1. temperatureCool the mixture in an ice-bath
  2. stirringAfter stirring overnight at room temperature
  3. filtrationfilter off the excess sodium hydroxide
  4. customRemove the solvent
  5. customby evaporation in vacuo
  6. customrecrystallise the resulting solid

출처 및 근거

ORD 기록
ord-4c711e232afa482e9afbc1e43a0ec931
출처 데이터셋
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06319930B1

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