1,3-Benzenedimethanamine → HCID 22917902, compound

HRID 1376664Notes

Reaction equation

C([C:4]12[CH2:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[C:11](O[C:14](=[O:15])[CH:5]21)=[O:12])C=C.[C:16]1([CH2:24][NH2:25])[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][NH2:23])[CH:17]=1>C1(C)C(C)=CC=CC=1>[C:16]1([CH2:24][N:25]2[C:11](=[O:12])[CH:6]3[CH:5]([C:4]4([CH2:11][CH:6]=[CH2:7])[CH2:10][CH:7]3[CH:8]=[CH:9]4)[C:14]2=[O:15])[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]2[C:11](=[O:12])[CH:6]3[CH:5]([C:4]4([CH2:9][CH:4]=[CH2:5])[CH2:10][CH:7]3[CH:8]=[CH:9]4)[C:14]2=[O:15])[CH:17]=1

Participants

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

additionwere charged
temperaturewith heating
customwhile separating
customremoving water
customproduced by the reaction by a water separator
customthe solvent, xylene, was removed by distillation
additionThereafter, the content of the flask was treated
stirringwhile stirring

Sources & evidence

ORD record: ord-1b33c0bd47b24161a6d71c32f5e81089
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663257

Reaction notes

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