Hydrochloric Acid → 5-Chloro-2-[(1-methylethyl)sulfanyl]benzonitrile

HRID 1015849Notes

Reaction equation

HRID 1015849 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][CH:12]([S-:14])[CH3:13].[Na+].Cl>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:14][CH:12]([CH3:13])[CH3:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 936535-Chloro-2-fluorobenzonitrileHCID 3470666Sodium 2-propanethiolate

Product 1

HCID 624939095-Chloro-2-[(1-methylethyl)sulfanyl]benzonitrileYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 5-chloro-2-fluorobenzonitrile (6.0 g) and sodium propane-2-thiolate (4.16 g) was stirred in N,N-dimethylformamide (30 ml) at room temperature for 18 hr. The reaction solution was treated with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give 5-chloro-2-[(1-methylethyl)sulfanyl]benzonitrile (7.26 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e18d3e0bd2634554ae1dd1c774298890
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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