Benzaldehyde, p-phenylthio- → 4-Phenylsulfanyl-benzaldehyde Oxime

HRID 498137Notes

Reaction equation

HRID 498137 reaction equation
[C:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:16][OH:17].Cl.C([O-])(=O)C.[Na+]>C(Cl)Cl.C(Cl)Cl.CC(C)=O.C(O)C.O>[C:1]1([S:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[N:16][OH:17])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 71023Benzaldehyde, p-phenylthio-HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 854453584-Phenylsulfanyl-benzaldehyde OximeYield 85.9%

Reagents, catalysts & solvents 4

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 21584124Propan-2-one--dichloromethane (1/1)Solvent

Procedure

To 4.20 g (19.6 mmol) of 4-phenylsulfanyl-benzaldehyde, 1.50 g (21.6 mmol) of H2NOH—HCl and 2.71 g (33.1 mmol) of sodium acetate are added 6.5 mL of H2O and 19.5 mL of ethanol. This reaction mixture is heated to reflux for 2 h. After adding H2O to dissolve the precipitated inorganic salt, ethanol is removed by evaporation in vacuo. The crude product is extracted twice with CH2Cl2. The CH2Cl2 layer is dried over anhydrous MgSO4 and then condensed. The residue is applied to column chromatography on silica gel with CH2Cl2 and CH2Cl2-acetone (10:1) as eluent. 3.86 g of white solid are obtained as the first fraction (86%). This product is assigned to be (E) oxime by 1H-NMR spectrum (CDCl3). δ [ppm]: 7.25 (d, 2H), 7.32-7.35 (m, 3H), 7.42 (d, 2H), 7.47 (d, 2H), 7.77 (s, 1H), 8.09 (s, 1H); 0.29 g of white solid are obtained as the second fraction (6.6%). This product is assigned to be (Z) oxime by 1H-NMR spectrum (CDCl3). δ [ppm]: 7.25 (d, 2H), 7.32-7.38 (m, 4H), 7.45 (d, 2H), 7.84 (d, 2H). 9.55 (broad s, 1H)

Workup

  1. temperatureThis reaction mixture is heated
  2. temperatureto reflux for 2 h
  3. customis removed by evaporation in vacuo
  4. extractionThe crude product is extracted twice with CH2Cl2
  5. dry with materialThe CH2Cl2 layer is dried over anhydrous MgSO4
  6. customcondensed

Sources & evidence

ORD record
ord-a058cafe054f422c9883db546bf78734
Source dataset
uspto-grants-2005_09
Patent number
US06949678B2

Reaction notes

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