1,5-Dichloroanthraquinone → 1,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

HRID 522936

反応式

HRID 522936 の反応式
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9](Cl)[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][NH:23][CH3:24]>O>[CH3:19][N:20]([CH3:25])[CH2:21][CH2:22][N:23]([CH3:24])[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([N:23]([CH2:22][CH2:21][N:20]([CH3:25])[CH3:19])[CH3:24])[CH:10]=[CH:11][CH:12]=3)[C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 67111,5-DichloroanthraquinoneHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

生成物 1

HCID 592291181,5-Bis((2-(dimethylamino)ethyl)(methyl)amino)anthracene-9,10-dione

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 1,5-dichloroanthraquinone (5.5 g, 20 mmol) and N,N,N′-trimethylethylenediamine (40 ml) was refluxed for 18 h. The mixture was cooled to room temperature, diluted with water (400 mL) and extracted with chloroform (2×200 mL). The combined organic layer was washed with water, brine, dried over MgSO4 and evaporated to dryness. The residue thus obtained was purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)] to provide Compound 9. Abs (max, PBS pH 7.4)=508 nm. The structure of Compound 9 is given below:

後処理

  1. temperaturewas refluxed for 18 h
  2. extractionextracted with chloroform (2×200 mL)
  3. washThe combined organic layer was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue thus obtained
  7. customwas purified by silica gel flash chromatography [CHCl3/MeOH/Et3N (44:5:1)]

出典と根拠

ORDレコード
ord-e3151e542a2f4975a8558c2400efa07e
出典データセット
uspto-grants-2016_05
特許番号
US09334281B2

関連ノート

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