Hydrochloric Acid → 5-Chloro-2-(ethylsulfanyl)benzonitrile

HRID 1015733Notes

Reaction equation

HRID 1015733 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH2:11]([S-:13])[CH3:12].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:13][CH2:11][CH3:12])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 936535-Chloro-2-fluorobenzonitrileHCID 4459711Sodium ethanethiolate

Product 1

HCID 624932485-Chloro-2-(ethylsulfanyl)benzonitrileYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 5-chloro-2-fluorobenzonitrile (5.83 g) and sodium ethanethiolate (3.47 g) was stirred in N,N-dimethylformamide (50 ml) at room temperature for 14 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 5-chloro-2-(ethylsulfanyl)benzonitrile (7.4 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-fd179971053e46cdae89d5405a4ef5ff
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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