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

HRID 447824Notes

Reaction equation

HRID 447824 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:11][S-:12].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12][CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 936535-Chloro-2-fluorobenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 598456935-Chloro-2-(methylthio)benzonitrileYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 5-chloro-2-fluorobenzonitrile (5.0 g) and sodium methanethiolate (2.48 g) was stirred in N,N-dimethylformamide (20 ml) at 60° C. for 1 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-(methylsulfanyl)benzonitrile (5.7 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-c7f62e6d76a043e59066f412b7b333cc
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

Loading…