1,3-Cyclohexadiene → 3a-(3,4-dichlorophenyl)-2-ethyl-3a,4,7,7a-tetrahydro-4,7-ethano-1H-isoindol-1,3(2H)-dione

HRID 371139

Reaction equation

HRID 371139 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10](=[O:17])[N:11]([CH2:15][CH3:16])[C:12](=[O:14])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:18]1[CH2:23][CH2:22][CH:21]=[CH:20][CH:19]=1>ClCCl.CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:20]4[CH2:21][CH2:22][CH:23]([CH:18]=[CH:19]4)[CH:13]2[C:12](=[O:14])[N:11]([CH2:15][CH3:16])[C:10]3=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 135195733-(3,4-dichlorophenyl)-1-ethyl-1H-pyrrole-2,5-dione

Product 1

HCID 135195663a-(3,4-dichlorophenyl)-2-ethyl-3a,4,7,7a-tetrahydro-4,7-ethano-1H-isoindol-1,3(2H)-dioneYield 57.4%

Reagents, catalysts & solvents 2

HCID 4139Methylene blue cationCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 7.5 g of the above maleimide, 2.25 g of 1,3-cyclohexadiene, and 10 mg of methylene blue in 25 ml of dichloromethane was heated at reflux for 5 hours, then an additional one ml of the diene was added and the solution was heated for 24 hours. The cooled reaction mixture was subjected to high pressure liquid chromatography on a silica gel column eluting with hexane:ethyl acetate (4:1) and gave 5.58 g of 3a-(3,4-dichlorophenyl)-2-ethyl-3a,4,7,7a-tetrahydro-4,7-ethano-1H-isoindol-1,3(2H)-dione as a white solid, mp 122°-126° C.

Workup

  1. temperatureat reflux for 5 hours
  2. temperaturethe solution was heated for 24 hours
  3. customThe cooled reaction mixture
  4. washeluting with hexane:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-6c8109afb7414cbd97405ce1beacba2f
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Linked notes

Loading…