P-Phenylenediamine → N,N'-(p-phenylene)-bis[3,4,5,6-tetrabromophthalimide]

HRID 236389

反応式

HRID 236389 の反応式
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([NH2:8])[CH:2]=1.[Br:9][C:10]1[C:11]([Br:23])=[C:12]([Br:22])[C:13]([Br:21])=[C:14]2[C:19](=[O:20])O[C:16](=[O:17])[C:15]=12>CN1C(=O)CCC1>[C:3]1([N:8]2[C:16](=[O:17])[C:15]3=[C:10]([Br:9])[C:11]([Br:23])=[C:12]([Br:22])[C:13]([Br:21])=[C:14]3[C:19]2=[O:20])[CH:4]=[CH:5][C:6]([N:7]2[C:19](=[O:20])[C:14]3=[C:13]([Br:21])[C:12]([Br:22])=[C:11]([Br:23])[C:10]([Br:9])=[C:15]3[C:16]2=[O:17])=[CH:1][CH:2]=1

参加物

4

反応物 2

HCID 7814P-PhenylenediamineHCID 12443Tetrabromophthalic anhydride

生成物 1

HCID 12422003N,N'-(p-phenylene)-bis[3,4,5,6-tetrabromophthalimide]

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒2 回

反応条件

温度
200 °C

実験手順

108 gms (1.0 mole) of p-phenylenediamine was dissolved in 1 liter of warm NMP under a nitrogen atmosphere and the solution filtered to remove suspended particles. This filtered solution was then added to a similarly prepared filtered solution of 928 gms (2.0 moles) of tetrabromophthalic anhydride in 2 liters of warm NMP in the apparatus described in Example 2. A mildly exothermic reaction took place and the mixture was further heated while stirring. At about 145° C., precipitation began. The quantity of brown precipitate increased with continued heating and a further 2 liters of NMP was added to facilitate stirring, the temperature being raised to 200° C. and maintained for 2 hours, before the mixture was allowed to cool. The precipitate was collected, washed with NMP, roughly dried and washed with acetone. The material was then stirred well with acetone, filtered and again washed before being dried overnight at 150° C. under vacuum. The product was a fine, rusty-gold precipitate with a melting point above 500° C. The yield was 486 gms (49%), the infrared spectrum having the characteristic imide structure, absorption bands at 1712s and 1765w cm-1. The compound was insoluble in water, methanol, ether, xylene, dimethyl sulphoxide and dimethyl acetamide.

後処理

  1. filtrationthe solution filtered
  2. customto remove
  3. additionThis filtered solution was then added to
  4. customa similarly prepared
  5. customA mildly exothermic reaction
  6. temperaturethe mixture was further heated
  7. customAt about 145° C., precipitation
  8. temperatureThe quantity of brown precipitate increased
  9. temperaturewith continued heating
  10. additiona further 2 liters of NMP was added
  11. stirringto facilitate stirring
  12. temperaturemaintained for 2 hours, before the mixture
  13. temperatureto cool
  14. customThe precipitate was collected
  15. washwashed with NMP
  16. customroughly dried
  17. washwashed with acetone
  18. stirringThe material was then stirred well with acetone
  19. filtrationfiltered
  20. washagain washed
  21. custombefore being dried overnight at 150° C. under vacuum
  22. customthe characteristic imide structure, absorption bands at 1712s and 1765w cm-1

出典と根拠

ORDレコード
ord-d023268cb2704454b9e08b7fc8b542e4
出典データセット
uspto-grants-1987_02
特許番号
US04644066

関連ノート

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