Diethyl Ether → HCID 19010307, compound

HRID 1741609Notes

Reaction equation

HRID 1741609 reaction equation
[C:1]([N:4]1[C:8](=[O:9])[C:7]([CH:11]([CH3:13])[CH3:12])([CH3:10])[N:6]=[C:5]1[C:14]1[N:23]=[C:22]([CH3:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1.CCOCC>C(Cl)Cl>[C:1]([N:4]1[C:8](=[O:9])[C:7]([CH:11]([CH3:13])[CH3:12])([CH3:10])[N:6]=[C:5]1[C:14]1[N+:23]([O-:33])=[C:22]([CH3:24])[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 19010354HCID 19010354, compound

Product 1

HCID 19010307HCID 19010307, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 29 g of methyl 2-(1-acetyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methylnicotinate and 28.7 g of 80% M-chloroperbenzoic acid in 250 mL of methylene chloride is stirred and heated at reflux for 31/2 hours. The reaction mixture is filtered, and the solid is thoroughly washed with methylene chloride. The combined filtrates are cooled and treated cautiously with saturated aqueous sodium bisulfite until a negative starch-iodide test is obtained. The mixture is again filtered, and the organic layer is washed with saturated sodium bicarbonate solution, dried, and concentrated in vacuo to give an oil. Trituration of this oil with ether affords the desired product as a pale yellow solid, mp 135°-138.5° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 31/2 hours
  3. filtrationThe reaction mixture is filtered
  4. washthe solid is thoroughly washed with methylene chloride
  5. temperatureThe combined filtrates are cooled
  6. additiontreated cautiously with saturated aqueous sodium bisulfite until a negative starch-iodide test
  7. customis obtained
  8. filtrationThe mixture is again filtered
  9. washthe organic layer is washed with saturated sodium bicarbonate solution
  10. customdried
  11. concentrationconcentrated in vacuo
  12. customto give an oil

Sources & evidence

ORD record
ord-788f1a407ed242e380151b83f937f7bf
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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