Melatonin → HCID 11090036, compound

HRID 382324

Reaction equation

HRID 382324 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]

Participants

6

Reactant 3

HCID 896MelatoninHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 11090036HCID 11090036, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-772d898a01774a5f803c6fe47044ad3a
Source dataset
uspto-grants-2001_10
Patent number
US06310074B1

Linked notes

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