1,3-Benzenedimethanamine → HCID 67061088, compound

HRID 1441119Notes

Reaction equation

HRID 1441119 reaction equation
[CH3:1][CH:2]1[C:11](=[O:12])O[C:8](=[O:9])[CH:3]1[CH2:4][CH:5]=[CH:6][CH3:7].C1(CN)C=CC=C(C[NH2:20])C=1>C1(C)C(C)=CC=CC=1>[CH3:1][CH:2]1[C:11](=[O:12])[NH:20][C:8](=[O:9])[CH:3]1[CH2:4][CH:5]=[CH:6][CH3:7]

Participants

4

Reactant 2

HCID 151331,3-BenzenedimethanamineHCID 54300175HCID 54300175, compound

Product 1

HCID 67061088HCID 67061088, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
200 °C

Procedure

To a 1000 ml flask replaced with nitrogen 257.4 g (1.26 mol) of allyl-bicyclo 2.2.1!hept-5-ene-2,3-dicarboxylic acid anhydride and 300 ml of xylene were charged. To the mixture was added 81.4 g (0.60 mol) of m-xylylenediamine over 1.5 hours with heating and stirring while refluxing xylene. The reaction was continued for 3 hours while separating and removing water produced by the reaction by a water separator, and then the solvent, xylene, was removed by distillation. Thereafter, the content of the flask was treated with heat at 200° C. under reduced pressure of 1 Torr for 1 hour while stirring, thus obtaining 301.8 g (yield: 99%) of the target N,N'-m-xylylene-bis(allyl-bicyclo 2.2.1!hept-5-ene-2,3-dicarboximide), of which the chemical structure is shown by the following formula 6!. This compound is hereinafter abbreviated to BANI-mX. ##STR10##

Workup

  1. customTo a 1000 ml flask replaced with nitrogen 257.4 g (1.26 mol) of allyl-bicyclo
  2. temperaturewith heating
  3. customwhile separating
  4. customremoving water
  5. customproduced by the reaction by a water separator
  6. customthe solvent, xylene, was removed by distillation
  7. additionThereafter, the content of the flask was treated
  8. stirringwhile stirring

Sources & evidence

ORD record
ord-ba172605fdf948348feb5151b21f035a
Source dataset
uspto-grants-1996_03
Patent number
US05502207

Reaction notes

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