Hydrogen Peroxide → HCID 23329209, compound

HRID 225156Notes

Reaction equation

HRID 225156 reaction equation
OO.[C:3]1([CH:9]2[O:11][C:10]2([C:17]#[N:18])[C:12]([O:14][CH2:15]C)=[O:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.[O-:21]P([O-])([O-])=O.[Na+].[Na+].[Na+]>CCOCC>[NH2:18][C:17]([C:10]1([C:12]([O:14][CH3:15])=[O:13])[CH:9]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[O:11]1)=[O:21]

Participants

6

Reactant 4

HCID 784Hydrogen Peroxide2×HCID 887MethanolHCID 24243Trisodium PhosphateHCID 13593322HCID 13593322, compound

Product 1

HCID 23329209HCID 23329209, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
45 °C

Procedure

100 ml of 30% hydrogen peroxide was added over a 20-minute period to a stirred mixture of 67 g of 1-phenyl-2-cyano-2-(ethoxycarbonyl)-1,2-epoxyethane (Reference II), 400 ml of methanol, 20 g of tribasic sodium phosphate (hydrate) and 8 g of 18 crown 6 ether at 25° C. The temperature was allowed to rise to 50° C. during the addition. The mixture then was cooled to 45° C. and 150 ml of the hydrogen peroxide solution was added over a 10-minute period. The temperature rose to 48° C. It was held there for one hour, then was raised to 60° C. and held there for 2 hours. The volatile materials were evaporated under reduced pressure. The residue was recrystallized from chloroform to give 8, mp: 175°-177° C.

Workup

  1. additionto rise to 50° C. during the addition
  2. customrose to 48° C
  3. temperaturewas raised to 60° C.
  4. waitheld there for 2 hours
  5. customThe volatile materials were evaporated under reduced pressure
  6. customThe residue was recrystallized from chloroform
  7. customto give 8, mp: 175°-177° C.

Sources & evidence

ORD record
ord-70ec0f12a3aa4404a7bf4d23cb1236c6
Source dataset
uspto-grants-1980_11
Patent number
US04235923

Reaction notes

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