p-Toluenesulfonic acid → HCID 66761019, compound

HRID 389522Notes

Reaction equation

HRID 389522 reaction equation
[Br:1][C:2]1[C:3]([S:12]C(C)(C)C)=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH:5]=[N:6]O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)CCC>[Br:1][C:2]1[C:3]2[S:12][N:6]=[CH:5][C:4]=2[CH:8]=[C:9]([F:11])[CH:10]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86662413HCID 86662413, compound

Product 1

HCID 66761019HCID 66761019, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-bromo-2-tert-butylsulfanyl-5-fluoro-benzaldehyde oxime (3.8 g, 12 mmol) and p-toluenesulfonic acid (1.1 g, 6.2 mmol) in n-butanol (60 mL) was heated to reflux for 16 h. The reaction mixture was then concentrated. The residue was treated with water and saturated aqueous sodium bicarbonate, then extracted with dichloromethane (3×20 mL). The combined organic fractions were washed with water, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (100% hexanes) afforded 900 mg (32%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.97 (s, 1H), 7.68 (dd, J=2, 6 Hz, 1H), 7.50 (dd, J=2, 6 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. concentrationThe reaction mixture was then concentrated
  4. additionThe residue was treated with water and saturated aqueous sodium bicarbonate
  5. extractionextracted with dichloromethane (3×20 mL)
  6. washThe combined organic fractions were washed with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by column chromatography (100% hexanes)

Sources & evidence

ORD record
ord-c903c113769a4ad4b13372035712267a
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…