Water → 5-Methoxy-2-(methylsulfanyl)benzonitrile

HRID 447818Notes

Reaction equation

HRID 447818 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:12][S-:13].[Na+].O>CN(C)C=O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]([S:13][CH3:12])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 27745462-Fluoro-5-methoxybenzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 668777365-Methoxy-2-(methylsulfanyl)benzonitrileYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 2-fluoro-5-methoxybenzonitrile (10 g) and sodium methanethiolate (5.1 g) was stirred in N,N-dimethylformamide (20 ml) at 60° C. for 3 hr. The reaction solution was treated with water, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate-hexane to give 5-methoxy-2-(methylsulfanyl)benzonitrile (8.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with 1N hydrochloric acid, aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fbc70185ca3d43d2a902ec6f49bc5d4d
Source dataset
uspto-grants-2013_07
Patent number
US08481569B2

Reaction notes

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