2,4-Dinitrophenol → HCID 10825027, compound

HRID 1451099Notes

Reaction equation

HRID 1451099 reaction equation
C1S[CH:5]([C:6]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:7]=2[NH:16][S:17]([CH3:20])(=[O:19])=[O:18])SCC1.CC[O:24]C(C)=O.CCCCCC.C1C([N+]([O-])=O)=CC([N+]([O-])=O)=C(O)C=1>CN(C)C=O.CC(C)=O.[Cu]=O.[Cu](Cl)Cl>[CH3:20][S:17]([NH:16][C:7]1[CH:8]=[CH:9][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:11][C:6]=1[CH:5]=[O:24])(=[O:19])=[O:18]

Participants

8

Reactant 3

HCID 14932,4-DinitrophenolHCID 10593784HCID 10593784, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10825027HCID 10825027, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 14829Copper oxideCatalystHCID 24014Cupric ChlorideCatalystHCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A sample of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde trimethylene mercaptal (7.66 g, 0.022 mol) dissolved in N,N-dimethylformamide (4.35 mL) and acetone (39.13 mL) was added over a 5-min period through a dropping funnel to a solution of copper (II) oxide (2.09 g, 0.026 mol), copper (II) chloride (7.0 g, 0.055 mol) in acetone (174.0 mL) and heated at reflux. After 2 h at reflux, thin-layer chromatography analysis (SiO2, EtOAc:hexane 1:1) showed disappearance of the starting material and the appearance of a new slightly higher Rf spot which gave a positive result when sprayed with 2,4-DNP. Upon cooling, the reaction was filtered through Celite and the cake was washed with 10% ethanol in dichloromethane. Water (125 mL) and dichloromethane (150 mL) were added to the filtrate. The layers were partitioned and the water layer extracted 2×100 mL dichloromethane. The combined organic layers were washed twice with water (100 mL), dried (Na2SO4), and filtered. Concentration of the filtrate gave a beige solid which was dried in vacuo to give 4.48 g (79%) of 2-(methanesulfonylamino)-5-(methoxycarbonyl)benzaldehyde, mp 161°-163° C. (ethanol).

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. temperatureAfter 2 h at reflux
  4. customthe appearance of a new slightly higher Rf spot which gave
  5. customa positive result when
  6. temperatureUpon cooling
  7. filtrationthe reaction was filtered through Celite
  8. washthe cake was washed with 10% ethanol in dichloromethane
  9. additionWater (125 mL) and dichloromethane (150 mL) were added to the filtrate
  10. customThe layers were partitioned
  11. extractionthe water layer extracted 2×100 mL dichloromethane
  12. washThe combined organic layers were washed twice with water (100 mL)
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. customConcentration of the filtrate gave a beige solid which
  16. customwas dried in vacuo

Sources & evidence

ORD record
ord-0953a01196a24ed9b92f0994ce3a095e
Source dataset
uspto-grants-1997_02
Patent number
US05602277

Reaction notes

Loading…