Benzyl Chloride → 3-(Benzylsulfanyl)aniline

HRID 2290045Notes

Reaction equation

HRID 2290045 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([SH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([S:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:3])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 315773-Aminothiophenol

Product 1

HCID 118443953-(Benzylsulfanyl)aniline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.), stirred slurry of 1.7 g of sodium hydride oil dispersion (60%) in 100 mL of dry THF, under argon, is added via cannula 4.95 g of 3-aminothiophenol in 5 mL of THF. After 5 min, 4.6 mL of benzyl chloride is added. The mixture is allowed to warm to room temperature and stirred for 18 h, then cooled to 0° C. and partitioned between water and diethyl ether. The organic phase is washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure. Flash chromatography of the residual oil on silica using 30% ethyl acetate in heptane provides 7.57 g of the title compound as a beige crystalline solid, which may be recrystallized from ether-hexane.

Workup

  1. temperaturecooled to 0° C.
  2. custompartitioned between water and diethyl ether
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-552ec561a7d54984b8c1bdb5978fbf27
Source dataset
uspto-grants-2000_07
Patent number
US06093732

Reaction notes

Loading…