Peracetic Acid → HCID 59001677, compound

HRID 1594362Notes

Reaction equation

HRID 1594362 reaction equation
[C:1]([NH2:13])(=[O:12])[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:14]([O-:17])(=O)[CH3:15].[Na+].[C:19](OO)(=O)[CH3:20].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[CH2:1]([NH:13][C:14](=[O:17])[CH2:15][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:19]=[CH2:20])[CH2:2][CH2:3][NH:13][C:1](=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11]

Participants

7

Reactant 4

HCID 6585Peracetic Acid2×HCID 24437Sodium SulfiteHCID 517045Sodium AcetateHCID 53633137HCID 53633137, compound

Product 1

HCID 59001677HCID 59001677, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

To a 100 mL, three-necked round bottom flask (fitted with a reflux condenser, addition funnel, and stir bar) was added undecenamide according to the above formula (10) (4.07 g, 10.0 mmol, 20.0 mmol double bonds) and methylene chloride (50 mL). To the addition funnel was added a solution of sodium acetate (0.17 g) in 32 wt % peracetic acid (5.05 mL of 32 wt %, 5.71 g of 32 wt %, 1.83 g peracetic acid, and 24.0 mmol peracetic acid). The peracetic acid solution was added dropwise over 20 minutes to the suspension of formula (10) in methylene chloride, which had been cooled to 15° C. The reaction mixture was stirred at 25° C. for one hour, during which time the amide dissolved/reacted. The reaction mixture was then heated at reflux for 15 hours. The reaction mixture was then cooled to 15° C. in an ice bath, after which a solution of sodium sulfite (3.02 g, 24.0 mmol) in water (30 mL) was added dropwise to the reaction mixture. The organic and aqueous layers were then separated. The organic solution was washed consecutively with equal volumes of water, 5% (w/v) NaCl (twice), and 5% (w/v) NaHCO3 (twice). The organic layer was then dried over MgSO4, filtered, and solvent was removed under reduced pressure to yield a white solid. The crude product was recrystallized from acetone (100 mL) to which water (1 mL) had been added. The recrystallized product was dried in vacuo at 25° C. for 4 hours. The thus obtained polyepoxy amide is represented by formula (11) shown below. Yield: 1.65 g (38%). M.P. 119-122° C. Epoxide equivalent weight (EEW): 224.6 g/mol epoxide (calculated EEW=219.3).

Workup

  1. customTo a 100 mL, three-necked round bottom flask (fitted with a reflux condenser, addition funnel, and stir bar)
  2. customdissolved/reacted
  3. temperatureThe reaction mixture was then heated
  4. temperatureat reflux for 15 hours
  5. temperatureThe reaction mixture was then cooled to 15° C. in an ice bath
  6. customThe organic and aqueous layers were then separated
  7. washThe organic solution was washed consecutively with equal volumes of water, 5% (w/v) NaCl (twice), and 5% (w/v) NaHCO3 (twice)
  8. dry with materialThe organic layer was then dried over MgSO4
  9. filtrationfiltered
  10. customsolvent was removed under reduced pressure
  11. customto yield a white solid
  12. customThe crude product was recrystallized from acetone (100 mL) to which water (1 mL)
  13. additionhad been added
  14. customThe recrystallized product was dried in vacuo at 25° C. for 4 hours

Sources & evidence

ORD record
ord-50a8d49aa45a4486ac2667322c45632f
Source dataset
uspto-grants-2007_11
Patent number
US07300986B2

Reaction notes

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