Triethylamine → 2-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1031815Notes

Reaction equation

HRID 1031815 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][CH:10]([N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[C:11]([OH:13])=O.P(C#N)(=O)(OCC)OCC.C(N(CC)CC)C>CN(C)C=O.O>[C:15]1(=[O:24])[N:14]([CH:10]2[CH2:9][CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:11]2=[O:13])[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]12

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 140106814-(2-Aminophenyl)-2-phthalimidobutyric acid

Product 1

HCID 140106802-(2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 80 ml of N,N-dimethylformamide is dissolved 10 g of 4-(2-aminophenyl)-2-phthalimidobutyric acid, and 6.7 g of diethyl phosphorocyanidate is added dropwise to the solution under ice-cooling with stirring. After the addition is complete, stirring is continued for 15 minutes, and 3.1 g of triethylamine is added dropwise to the mixture under ice cooling, followed by stirring under ice-cooling for 45 minutes and then at room temperature for 30 minutes. The reaction solution is diluted with 200 ml of water, followed by stirring for 1 hour, and the crystals, which separate out, are collected by filtration, dried and added to 100 ml of ethanol, followed by heating. After the solution is concentrated to about half of the original volume, the colorless prisms which separate out are collected by filtration to give 8.3 g of 3-phthalimido-1,3,4,5-tetrahydro-1-benzazepin-2-one. m.p. 261°-263° C.

Workup

  1. additionis added dropwise to the solution under ice-
  2. temperaturecooling
  3. additionAfter the addition
  4. stirringstirring
  5. stirringby stirring under ice-
  6. temperaturecooling for 45 minutes
  7. waitat room temperature for 30 minutes
  8. stirringby stirring for 1 hour
  9. customthe crystals, which separate out
  10. filtrationare collected by filtration
  11. customdried
  12. additionadded to 100 ml of ethanol
  13. temperatureby heating
  14. concentrationAfter the solution is concentrated to about half of the original volume
  15. customthe colorless prisms which separate out
  16. filtrationare collected by filtration

Sources & evidence

ORD record
ord-b643f1f8dd0f4cd7b5a7e4794872bcf7
Source dataset
uspto-grants-1990_09
Patent number
US04954625

Reaction notes

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