2-Methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile → 2-Mercapto-4-(4-trifluoromethylphenyl)benzonitrile

HRID 25299Notes

Reaction equation

HRID 25299 reaction equation
C[S:2]([C:4]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])=O>FC(F)(F)C(OC(=O)C(F)(F)F)=O>[SH:2][C:4]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

3

Reactant 1

HCID 221709512-Methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile2×

Product 1

HCID 121376372-Mercapto-4-(4-trifluoromethylphenyl)benzonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 9845Trifluoroacetic anhydrideSolvent

Procedure

2.2 g (7.1 mmol) of 2-methylsulfinyl-4-(4-trifluoromethylphenyl)benzonitrile prepared in (b) was stirred in 15 ml of trifluoroacetic anhydride at room temperature for 12 hours, and the low-boiling matters were distilled off under reduced pressure. 50 ml of methanol and 3 g of 20% aqueous potassium hydroxide were added to the residue, and the reaction was carried out for 1 hour. The solvent was distilled off under reduced pressure, and the residue was mixed with 5% aqueous sulfuric acid and extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.0 g of 2-mercapto-4-(4-trifluoromethylphenyl)benzonitrile (yield 51.0%), which was used in Example 1 as the starting material.

Workup

  1. distillationthe low-boiling matters were distilled off under reduced pressure
  2. addition50 ml of methanol and 3 g of 20% aqueous potassium hydroxide were added to the residue
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionthe residue was mixed with 5% aqueous sulfuric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-34368fc06629473d81e732cee37088b2
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Reaction notes

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