Hydrochloric Acid → HCID 12282095, compound

HRID 1013965Notes

Reaction equation

HRID 1013965 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-cfb9cc1bc9e743b88ad19f5b341b1349
Source dataset
uspto-grants-2011_07
Patent number
US07982044B2

Reaction notes

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