Acetone → N,N'-1,3-Phenylenedimaleimide

HRID 262417

반응식

HRID 262417 반응식
[C:1]1(=[O:7])O[C:4](=[O:5])[CH:3]=[CH:2]1.[C:8]1([NH2:15])[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1.O.O.O.O.O.O.[Cl-].[Mg+2].[Cl-].C(O[C:29](=[O:31])[CH3:30])(=O)C.[CH3:32][C:33](C)=[O:34]>C(N(CC)CC)C>[C:8]1([N:15]2[C:1](=[O:7])[CH:2]=[CH:3][C:4]2=[O:5])[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[C:29](=[O:31])[CH:30]=[CH:32][C:33]2=[O:34])[CH:9]=1

참가 물질

7

반응물 5

HCID 180Acetone2회HCID 7918Acetic AnhydrideHCID 7923Maleic AnhydrideHCID 7935M-PhenylenediamineHCID 24644Magnesium chloride hexahydrate

생성물 1

HCID 18156N,N'-1,3-Phenylenedimaleimide수율 92%

시약·촉매·용매 1

HCID 8471Triethylamine용매

반응 조건

온도
40 °C

실험 절차

A flask was equipped as in Example 1. To a solution of maleic anhydride (1.92 parts) in 4.8 parts acetone was added a solution of 1 part m-phenylenediamine, 0.32 part triethylamine and 1.6 parts acetone over a 15-minute period. A precipitate formed during that time. The heterogeneous reaction mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.08 part) and 2.44 parts acetic anhydride were added all at once. The temperature was raised to 50° C. and maintained for 3 hours. After 30 minutes, the reaction mixture became homogeneous and amber in color. Five minutes later, the product began to precipitate. At the end of the reaction time, the mixture was cooled and 12 parts water added. The precipitated product was collected by vacuum filtration, washed with water, and dried for 24 hours at 60° C. in a vacuum oven. A 92% yield of N,N'-m-phenylenedimaleimide, m.p. 204°-205° C., was obtained.

후처리

  1. customA flask was equipped as in Example 1
  2. customA precipitate formed during that time
  3. temperatureThe temperature was raised to 50° C.
  4. temperaturemaintained for 3 hours
  5. customFive minutes
  6. customto precipitate
  7. temperatureAt the end of the reaction time, the mixture was cooled
  8. addition12 parts water added
  9. filtrationThe precipitated product was collected by vacuum filtration
  10. washwashed with water
  11. customdried for 24 hours at 60° C. in a vacuum oven

출처 및 근거

ORD 기록
ord-dab1331b97f54aa09ed037a702a64e79
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04154737

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