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

HRID 323979Notes

Reaction equation

HRID 323979 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f7c39551548f4886aa24f4e6d5c35a9f
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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