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

HRID 447838Notes

Reaction equation

HRID 447838 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-335dd0ffdb9d42afbf7618b7a5188e88
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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