4-Aminothiophenol → HCID 19980026, compound

HRID 1461205Notes

Reaction equation

HRID 1461205 reaction equation
[Na].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Cl[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17]>C(O)C>[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 145104-AminothiophenolHCID 748286-Chloro-1-hexanolHCID 5360545Sodium2×

Product 1

HCID 19980026HCID 19980026, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (24 g, 1.05 mol) was added cautiously, in small portions, to 1 liter of stirred absolute ethanol under nitrogen. When the sodium has dissolved, 125 g (1.0 mol) of 4-aminothiophenol was added slowly. 6-Chlorohexanol (143 g, 1.05 mol) was added in small portions, and the resulting mixture was heated at reflux with stirring for one hour. The reaction mixture was cooled, filtered, and the ethanol was evaporated at reduced pressure. The residue was taken up in dichloromethane, and the solution was washed with water, with 5% NaHCO3 and again with water. The organic layer was dried (Na2SO4), concentrated, and the solid residue was recrystallized from ethanol. A pale yellow solid was obtained, mass 156 g.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customthe ethanol was evaporated at reduced pressure
  6. washthe solution was washed with water, with 5% NaHCO3 and again with water
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated
  9. customthe solid residue was recrystallized from ethanol
  10. customA pale yellow solid was obtained

Sources & evidence

ORD record
ord-5632ea643d464ebd911075686a73bd4a
Source dataset
uspto-grants-1991_12
Patent number
US05075043

Reaction notes

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