Hydrochloric Acid → 2-(Ethylsulfanyl)-5-methylbenzonitrile

HRID 1013996Notes

Reaction equation

HRID 1013996 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5].[CH2:11]([S-:13])[CH3:12].[Na+].Cl>CN(C)C=O>[CH2:11]([S:13][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[C:4]#[N:5])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27745842-Fluoro-5-methylbenzonitrileHCID 4459711Sodium ethanethiolate

Product 1

HCID 668771452-(Ethylsulfanyl)-5-methylbenzonitrileYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 2-fluoro-5-methylbenzonitrile (7.5 g) and sodium ethanethiolate (4.9 g) was stirred in N,N-dimethylformamide (30 ml) at room temperature for 3 hr. The reaction solution was treated with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 2-(ethylsulfanyl)-5-methylbenzonitrile (8.57 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-aadc41946eae4174ad87e33ec572923c
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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