Ethanethiol → 4-Chloro-2-ethylsulfanyl-6-methyl-benzonitrile

HRID 515144Notes

Reaction equation

HRID 515144 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].Cl[C:7]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([CH3:16])[C:8]=1[C:9]#[N:10]>O1CCCC1>[Cl:15][C:13]1[CH:12]=[C:11]([CH3:16])[C:8]([C:9]#[N:10])=[C:7]([S:5][CH2:3][CH3:4])[CH:14]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 28009652,4-Dichloro-6-methylbenzonitrile

Product 1

HCID 866997224-Chloro-2-ethylsulfanyl-6-methyl-benzonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% suspension in mineral oil, 0.54 g, 13.6 mmol) in dry tetrahydrofuran (15 ml) is added ethanethiol (0.36 ml, 4.84 mmol) at 0° C. After effervescence has ceased, a solution of 2,4-dichloro-6-methyl-benzonitrile (1.00 g, 5.37 mmol) in THF (5 ml) is added drop wise at 0° C. The reaction mixture is stirred at RT for 16 h. After completion of the reaction (monitored by TLC), the reaction is quenched with ice water and extracted with ethyl acetate (3×30 ml). The organic layer is washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 5% dichloromethane/hexane) to yield 4-chloro-2-ethylsulfanyl-6-methyl-benzonitrile (0.50 g, 2.37 mmol, 44%).

Workup

  1. customAfter completion of the reaction (monitored by TLC)
  2. customthe reaction is quenched with ice water
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe organic layer is washed with saturated sodium hydrogen carbonate solution (20 ml), water (20 ml), brine (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto get the crude product, which
  8. customis purified by column chromatography (silica gel, 5% dichloromethane/hexane)

Sources & evidence

ORD record
ord-c9bd734663b34e4fa7c70b70740dc97b
Source dataset
uspto-grants-2015_08
Patent number
US09108936B2

Reaction notes

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