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

HRID 522936노트

반응식

HRID 522936 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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:

후처리

  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)]

출처 및 근거

ORD 기록
ord-e3151e542a2f4975a8558c2400efa07e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334281B2

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