p-Toluenesulfonic acid → HCID 66759851, compound

HRID 389469Notes

Reaction equation

HRID 389469 reaction equation
[Br:1][C:2]1[C:3]([S:14]C(C)(C)C)=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[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:14][N:6]=[CH:5][C:4]=2[CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86662402HCID 86662402, compound

Product 1

HCID 66759851HCID 66759851, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-bromo-2-tert-butylsulfanyl-5-nitro-benzaldehyde oxime (1.98 g, 5.97 mmol) and p-toluenesulfonic acid (567 mg, 2.98 mmol) in n-butanol (20 mL) was heated to reflux for 16 h. The reaction mixture was cooled and concentrated. The residue was treated with water followed by saturated sodium bicarbonate solution and then was 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 (20% ethyl acetate:hexanes) afforded 1.0 g (65%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 9.21 (s, 1H), 8.95 (s, 1H), 8.59 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. additionThe residue was treated with water
  6. extractionwas extracted with dichloromethane (3×20 mL)
  7. washThe combined organic fractions were washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification by column chromatography (20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f69367b7c63045f3ac6245b35abda43c
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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