Peracetic Acid → HCID 59001674, compound

HRID 1594360Notes

Reaction equation

HRID 1594360 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+]>C(Cl)Cl.O>[CH2:1]([NH:13][C:14](=[O:17])[CH2:15][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:19]=[CH2:20])[CH2:2][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 517045Sodium AcetateHCID 23665763Sodium BisulfiteHCID 53633137HCID 53633137, compound

Product 1

HCID 59001674HCID 59001674, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
15 °C

Procedure

To a 500 mL, three-necked round bottom flask (fitted with a reflux condenser, addition funnel, and stir bar) was added undecenamide according to the above formula (8) (8.90 g, 22.7 mmol, 45.3 mmol double bonds), sodium acetate (0.63 g), and methylene chloride (170 mL). To the addition funnel was added 32 wt % peracetic acid (19.1 mL of 32 wt %, 21.6 g of 32 wt %, 6.91 g of peracetic acid, and 90.9 mmol of peracetic acid). The peracetic acid solution was added dropwise over 20 minutes to the suspension of formula (8) 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 16 hours. The reaction mixture was then cooled to 15° C. in an ice bath, after which a solution of 60% (w/v) sodium bisulfite (9.44 g, 90.8 mmol) in water (200 mL) was added dropwise to the reaction mixture. A white solid/gel precipitated from solution. The solid was collected via suction filtration. The aqueous and organic phases were discarded. The crude product was recrystallized from a 2:1 mixture of acetone/ethanol (400 mL), then dried in vacuo at 25° C. for 16 hours. The thus obtained polyepoxy amide is represented by formula (9) shown below. Yield: 5.93 g (61%). Epoxide equivalent weight (EEW): 218.8 g/mol epoxide (calculated EEW=212.3).

Workup

  1. customTo a 500 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 16 hours
  5. temperatureThe reaction mixture was then cooled to 15° C. in an ice bath
  6. customA white solid/gel precipitated from solution
  7. filtrationThe solid was collected via suction filtration
  8. customThe crude product was recrystallized from a 2:1 mixture of acetone/ethanol (400 mL)
  9. customdried in vacuo at 25° C. for 16 hours

Sources & evidence

ORD record
ord-afe64314b3544413933971694d2cb4c0
Source dataset
uspto-grants-2007_11
Patent number
US07300986B2

Reaction notes

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