Hydrochloric Acid → HCID 12282095, compound

HRID 1015821Notes

Reaction equation

HRID 1015821 reaction equation
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:14][S-:15].[Na+].Cl>CN(C)C=O>[CH3:14][S:15][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 12282095HCID 12282095, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(Step 1) A mixture of 2-fluoro-5-(trifluoromethyl)benzonitrile (10 g) and sodium methanethiolate (4.08 g) was stirred in N,N-dimethylformamide (30 ml) at 80° C. for 14 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 2-(methylsulfanyl)-5-(trifluoromethyl)benzonitrile (7.71 g) as a solid.

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-44693660c73c440c943e3aa89ae82923
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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