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

HRID 429776
Notes
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Reaction equation

HRID 429776 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 896MelatoninHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

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

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4c711e232afa482e9afbc1e43a0ec931
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06319930B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes