N-Phthaloylglycine → 2-[(3-Ethyl-1,2,4-oxadiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1710187Notes

Reaction equation

HRID 1710187 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1(=[O:27])[N:17]([CH2:18][C:19]([OH:21])=O)[C:16](=[O:22])[C:15]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:14]12.[C:28](=[N:32]O)([NH2:31])[CH2:29][CH3:30]>O1CCCC1>[CH2:29]([C:28]1[N:32]=[C:19]([CH2:18][N:17]2[C:13](=[O:27])[C:14]3=[CH:26][CH:25]=[CH:24][CH:23]=[C:15]3[C:16]2=[O:22])[O:21][N:31]=1)[CH3:30]

Participants

5

Reactant 3

HCID 20825N-PhthaloylglycineHCID 682631,1'-CarbonyldiimidazoleHCID 4092053N-Hydroxypropionimidamide

Product 1

HCID 140319642-[(3-Ethyl-1,2,4-oxadiazol-5-yl)methyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 26.0 g of carbonyldimidazole in 250 ml of THF is added to a solution of 65.7 g of phthalimidoacetic acid in 500 ml of tetrahydrofuran (THF) (abs.) at 40° C. After about 1 hour, no generation of gas can be detected any longer. A solution of 28.2 propioamidoxime in 50 ml of THF is now added and stirred for 24 hours at room temperature. After filtering off of the precipitate the filtrate is concentrated in a vacuum and refluxed on a water separator for 6 hours after addition of 500 ml of dry xylene. The still hot solution is separated from the oily residue and concentrated in a vacuum. After crystallization from ethanol, 31.5 g of phthalimide with a melting point of 106-107° C. (76.5% relative to carbonyldiimidazole) is obtained.

Workup

  1. filtrationAfter filtering off of the precipitate the filtrate
  2. concentrationis concentrated in a vacuum
  3. temperaturerefluxed on a water separator for 6 hours
  4. additionafter addition of 500 ml of dry xylene
  5. customThe still hot solution is separated from the oily residue
  6. concentrationconcentrated in a vacuum
  7. customAfter crystallization from ethanol, 31.5 g of phthalimide with a melting point of 106-107° C. (76.5% relative to carbonyldiimidazole)
  8. customis obtained

Sources & evidence

ORD record
ord-2607a8f8b91144b4be15b6005facf006
Source dataset
uspto-grants-1990_08
Patent number
US04952698

Reaction notes

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