3,3'-Diaminobenzidine → 3,3'-Diaminobenzidine tetraisopropanimine

HRID 456363

反応式

HRID 456363 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[C:2](=[NH:1])([CH3:3])[CH3:7].[C:2](=[NH:1])([CH3:3])[CH3:7].[C:2](=[NH:1])([CH3:3])[CH3:7].[C:2](=[NH:1])([CH3:3])[CH3:7].[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([NH2:16])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8]

参加物

4

反応物 2

HCID 70713,3'-DiaminobenzidineHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 865942123,3'-Diaminobenzidine tetraisopropanimine収率 76%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

In a 200-ml flask equipped with a Soxhlet extractor including molecular sieves 4A as a dehydrating agent, a stirrer, a condenser and a thermometer were placed 21.4 g (100 mmol) of 3,3′-diaminobenzidine, 100 ml of acetone and 0.95 g (5 mmol) of p-toluenesulfonic acid monohydrate, followed by heating under reflux in a nitrogen atmosphere for 3 hours. After cooling to room temperature, acetone was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with water and 10% aqueous sodium carbonate solution to remove a residual acid component. Ethyl acetate was removed from the solution under reduced pressure, and the residue was purified by silica gel chromatography to yield 28.5 g (76 mmol) of the target 3,3′-diaminobenzidine tetraisopropanimine [N,N′,N″,N′″-tetraisopropylidene-3,4,3′,4′-biphenyltetramine] in a yield of 76%.

後処理

  1. customIn a 200-ml flask equipped with a Soxhlet extractor
  2. temperatureby heating
  3. temperatureunder reflux in a nitrogen atmosphere for 3 hours
  4. customacetone was removed under reduced pressure
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with water and 10% aqueous sodium carbonate solution
  7. customto remove a residual acid component
  8. customEthyl acetate was removed from the solution under reduced pressure
  9. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-ae0ec5721e654043af8dd4f1b652492d
出典データセット
uspto-grants-2007_03
特許番号
US07186454B2

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