Nitric Acid → HCID 57687233, compound

HRID 1443465Notes

Reaction equation

HRID 1443465 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH:12]=[CH2:13])(=[O:11])=[O:10])=[C:4]([CH3:14])[CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([N+:15]([O-:17])=[O:16])=[CH:6][C:5]([O:8][S:9]([CH:12]=[CH2:13])(=[O:11])=[O:10])=[C:4]([CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 57687198HCID 57687198, compound

Product 1

HCID 57687233HCID 57687233, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

Compound 105 (33.2 g, 142 mmol) was dissolved in cold concentrated sulphuric acid (70 ml) and 98% nitric acid (9.8 g) was added drop wise while cooling to keep the temperature below 10° C. The mixture was stirred for one hour at about 5° C. The mixture was added to ice water and extracted three times with ethyl acetate. The organic phase was washed twice with brine, dried with sodium sulphate and evaporated under reduced pressure. The product was isolated by column chromatography on silica gel eluted with hexane-ethyl acetate.

Workup

  1. temperaturewhile cooling
  2. customthe temperature below 10° C
  3. extractionextracted three times with ethyl acetate
  4. washThe organic phase was washed twice with brine
  5. dry with materialdried with sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe product was isolated by column chromatography on silica gel
  8. washeluted with hexane-ethyl acetate

Sources & evidence

ORD record
ord-b81627113bf84bd79f55f367d2009bf7
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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