1,3-Cycloheptadiene → HCID 13519567, compound

HRID 371141Notes

Reaction equation

HRID 371141 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([N:12]([CH3:16])[C:13](=[O:15])[CH:14]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:17]1[CH2:23][CH2:22][CH2:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]23[CH:19]4[CH2:20][CH2:21][CH2:22][CH:23]([CH:17]=[CH:18]4)[CH:14]2[C:13](=[O:15])[N:12]([CH3:16])[C:10]3=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 199691,3-CycloheptadieneHCID 202744143-(3,4-Dichlorophenyl)-1-methyl-1H-pyrrole-2,5-dione

Product 1

HCID 13519567HCID 13519567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
180 °C

Procedure

A mixture of 0.7 g (0.0027 mole) of 2-(3,4-dichlorophenyl-N-methylmaleimide and 5.0 g (0.05 mole) of 1,3-cycloheptadiene in a pressure vessel was heated in an oil bath at a bath temperature of 180° C. for 24 hours. The reaction vessel was cooled to room temperature and the contents were dissolved in and removed with the aid of dichloromethane and acetone. The solution was concentrated in vacuo and gave a tacky glass. The glass was dissolved in dichloromethane and filtered through hydrous magnesium silicate. The filtrate was again concentrated in vacuo and gave a glass. The glass was dissolved in dichloromethane and was chromatographed on a Waters Prep 500A LC, using a silica gel column and eluting with 10% ethyl acetate/hexane and gave 0.56 g of 3a-(3,4-dichlorophenyl)-3a,4,7,7a-tetrahydro-2-methyl-4,7-propano-1H-isoindol-1,3(2H)-dione as a yellow glass, mp 110°-115° C., mass spectrum, m/e 349.

Workup

  1. temperatureThe reaction vessel was cooled to room temperature
  2. dissolutionthe contents were dissolved in and
  3. customremoved with the aid of dichloromethane and acetone
  4. concentrationThe solution was concentrated in vacuo
  5. customgave a tacky glass
  6. filtrationfiltered through hydrous magnesium silicate
  7. concentrationThe filtrate was again concentrated in vacuo
  8. customgave a glass
  9. customwas chromatographed on a Waters Prep 500A LC
  10. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1d17b9c8fa1145739bde1fd2a236a925
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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