1-Hexanethiol → methyl N-[1-(4-hexylthiomethylphenyl)-1-methylethyl]carbamate

HRID 323979

Reaktionsgleichung

Reaktionsgleichung von HRID 323979
[CH2:1]([SH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([NH:21][C:22](=[O:25])[O:23][CH3:24])([CH3:20])[CH3:19])=[CH:14][CH:13]=1>CN(C=O)C>[CH2:1]([S:7][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([NH:21][C:22](=[O:25])[O:23][CH3:24])([CH3:20])[CH3:19])=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Komponenten

5

Edukt 3

HCID 81061-HexanethiolHCID 24758Sodium hydrideHCID 18349698methyl N-(1-(4-bromomethylphenyl)-1-methylethyl]carbamate

Produkt 1

HCID 18349621methyl N-[1-(4-hexylthiomethylphenyl)-1-methylethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 1-hexanethiol (4.89 g) in DMF (15 ml) was added to a suspension of sodium hydride (1.66 g, 60% dispersion in mineral oil) in DMF (35 ml) over 15 minutes with stirring under nitrogen. The mixture was stirred at ambient temperature for 3 hours and then heated on a steam bath for 15 minutes. A solution of methyl N-[1-(4-bromomethylphenyl)-1- methylethyl]-carbamate (11.85 g) in DMF (50 ml) was added to this mixture, dropwise, over 10 minutes, at 20° C., with stirring. The mixture was stirred at ambient temperature for 18 hours and then quenched with saturated potassium carbonate solution (100 ml). The mixture was diluted with water and extracted with ether to give methyl N-[1-(4-hexylthiomethylphenyl)-1-methylethyl]carbamate as an oil.

Aufarbeitung

  1. stirringThe mixture was stirred at ambient temperature for 3 hours
  2. temperatureheated on a steam bath for 15 minutes
  3. stirringat 20° C., with stirring
  4. stirringThe mixture was stirred at ambient temperature for 18 hours
  5. customquenched with saturated potassium carbonate solution (100 ml)
  6. additionThe mixture was diluted with water
  7. extractionextracted with ether

Quellen und Nachweise

ORD-Eintrag
ord-f7c39551548f4886aa24f4e6d5c35a9f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06215001B1

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