Water → 3,3'-Diamino-4,4'-di-2-furoylaminobiphenyl

HRID 49749

반응식

HRID 49749 반응식
O.[N+:2]([C:5]1[CH:6]=[C:7]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([C:28]3[O:29][CH:30]=[CH:31][CH:32]=3)=[O:27])=[C:21]([N+:33]([O-])=O)[CH:20]=2)[CH:8]=[CH:9][C:10]=1[NH:11][C:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)=[O:13])([O-])=O.[Cl-].[NH4+].[In]>C(O)C.CN1CCCC1=O>[NH2:33][C:21]1[CH:20]=[C:19]([C:7]2[CH:8]=[CH:9][C:10]([NH:11][C:12]([C:14]3[O:15][CH:16]=[CH:17][CH:18]=3)=[O:13])=[C:5]([NH2:2])[CH:6]=2)[CH:24]=[CH:23][C:22]=1[NH:25][C:26]([C:28]1[O:29][CH:30]=[CH:31][CH:32]=1)=[O:27]

참가 물질

7

반응물 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 5359967IndiumHCID 227415993,3'-Dinitro-4,4'-di-2-furoylaminobiphenyl

생성물 1

HCID 227416023,3'-Diamino-4,4'-di-2-furoylaminobiphenyl수율 23.3%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

Into a separable flask equipped with a stirrer and a reflux condenser cooled with water, 7.4 g of 3,3′-dinitro-4,4′-di-2-furoylaminobiphenyl, 100 ml of N-methyl-2-pyrrolidone and 75 ml of ethyl alcohol were placed. After adding 40 ml of a saturated aqueous solution of ammonium chloride, 25.6 g of powder of indium metal was added to the prepared solution. The obtained mixture was stirred at 80° C. for 1 hour. After the reaction solution was cooled to the room temperature, the solid substance was removed by filtration. The filtrate was concentrated to about one half at a reduced pressure. To the concentrated filtrate, 300 ml of water was added and the formed solid substance was separated by filtration to obtain 2.9 g of a crude product. The crude product was purified in accordance with the silica gel column chromatography to obtain 1.5 g of 3,3′-diamino-4,4′-di-2-furoylaminobiphenyl. The yield of the isolated product was 23%. This product was recrystallized from N-methyl-2-pyrrolidone/ethyl acetate (the volume ratio: 25/75) and needle crystals having a decomposition temperature of 256 to 259° C. were obtained.

후처리

  1. customInto a separable flask equipped with a stirrer and a reflux condenser
  2. additionwas added to the prepared solution
  3. temperatureAfter the reaction solution was cooled to the room temperature
  4. customthe solid substance was removed by filtration
  5. concentrationThe filtrate was concentrated to about one half at a reduced pressure
  6. additionTo the concentrated filtrate, 300 ml of water was added
  7. customthe formed solid substance was separated by filtration
  8. customto obtain 2.9 g of a crude product
  9. customThe crude product was purified in accordance with the silica gel column chromatography

출처 및 근거

ORD 기록
ord-70a34d2cf4ca4b2c893e159113b9d888
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06709804B2

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