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

HRID 49749

反応式

HRID 49749 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-70a34d2cf4ca4b2c893e159113b9d888
出典データセット
uspto-grants-2004_03
特許番号
US06709804B2

関連ノート

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