Hydroxyamine hydrochloride → 3-Bromo-2-tert-butylsulfanyl-4-iodo-benzaldehyde oxime

HRID 389476Notes

Reaction equation

HRID 389476 reaction equation
[Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=O.Cl.[NH2:17][OH:18]>C(O)C.O>[Br:1][C:2]1[C:3]([S:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[N:17][OH:18]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 866624043-Bromo-2-(tert-butylthio)-4-iodobenzaldehyde

Product 1

HCID 866624053-Bromo-2-tert-butylsulfanyl-4-iodo-benzaldehyde oximeYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-2-tert-butylsulfanyl-4-iodo-benzaldehyde (1.5 g, 3.8 mmol) and hydroxylamine hydrochloride in ethanol (20 mL) and water (4 mL) was heated to reflux for 2 h. The reaction mixture was cooled and concentrated. The residue was treated with water (40 mL) and then saturated aqueous sodium bicarbonate solution until the pH was ˜8.0. The mixture was extracted with ethyl acetate (2×40 mL). The combined organic fractions were dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (25% ethyl acetate:hexanes) afforded 1.1 g (70%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.34 (s, 9H), 7.41 (d, J=8.7 Hz, 1H), 7.77 (d, J=8.7 Hz, 1H), 8.47 (s, 1H), 8.51 (br. s, 1H); MS (ESI): 414, 416 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. additionThe residue was treated with water (40 mL)
  6. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
  7. dry with materialThe combined organic fractions were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by column chromatography (25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-48b8729f3e3a4ee690b0dfcbec954363
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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