Benzylmaleimide → HCID 20389909, compound

HRID 426764Notes

Reaction equation

HRID 426764 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH2:17]([N:24]1[C:28](=[O:29])[CH:27]=[CH:26][C:25]1=[O:30])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O.C(Cl)Cl>[CH2:17]([N:24]1[C:28](=[O:29])[CH:27]2[CH:26]([C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)([OH:5])[C:3]3[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:2]=3[CH2:1]2)[C:25]1=[O:30])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 74204BenzylmaleimideHCID 256066(2,5-Dimethylphenyl)(phenyl)methanone

Product 1

HCID 20389909HCID 20389909, compoundYield 52.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 35 g of 2,5-dimethylbenzophenone and 31.5 g of N-benzylmaleimide in 500 cc of acetone or methylene chloride is irradiated with a mercury high pressure lamp through a pyrex filter, until all the material has reacted (20 to 130 hours), filtration and concentration by evaporation are then effected. After crystallization from ether, the residue yields 35 g of 2-benzyl-3a,4,9,9a-tetrahydro-6-methyl-4-phenyl-benz[f]isoindolin-4-ol-1,3-dione, having a M.P. of 162-164°, which are dissolved in 170 cc of trifluoroacetic acid. The solution is stirred at 25° for 3 hours and concentrated by evaporation. After crystallization from methylene chloride/methanol, the residue yields 30 g of (9aRS)-2-benzyl-9,9a-dihydro-6-methyl-4-phenyl-benz[f]isoindoline-1,3-dione, having a M.P. of 156°-158°.

Workup

  1. filtrationfilter, until all the material
  2. customhas reacted
  3. filtration(20 to 130 hours), filtration and concentration
  4. customby evaporation
  5. customAfter crystallization from ether

Sources & evidence

ORD record
ord-1c209af8a5224b3dab6f344c11377980
Source dataset
uspto-grants-1979_10
Patent number
US04171369

Reaction notes

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