1,5-Dichloroanthraquinone → 1-Chloro-5-(2-(dimethylamino)ethylamino)anthracene-9,10-dione

HRID 522937

反応式

HRID 522937 の反応式
Cl[C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[C:9]([Cl:17])[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]([CH3:24])[CH2:21][CH2:22][NH2:23]>CN(C)C(=O)C>[Cl:17][C:9]1[C:8]2[C:7](=[O:18])[C:6]3[C:15](=[C:2]([NH:23][CH2:22][CH2:21][N:20]([CH3:24])[CH3:19])[CH:3]=[CH:4][CH:5]=3)[C:14](=[O:16])[C:13]=2[CH:12]=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 67111,5-DichloroanthraquinoneHCID 66053N,N-Dimethylethylenediamine

生成物 1

HCID 143201251-Chloro-5-(2-(dimethylamino)ethylamino)anthracene-9,10-dione収率 16.9%

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

A mixture of 1,5-dichloro anthraquinone (5.0 g, 18.0 mmol), N,N-dimethylacetamide (30 mL) and N,N-dimethylethylenediamine (2 mL, 18 mmol) was stirred at room temperature for 1 hour and then heated in an oil bath (T=100° C.) for 45 minutes. Reaction mixture was cooled and filtered. To the filtrate petroleum ether (50 mL) was added and combined mixture was stirred at 4° C. over night. Precipitated solid was removed by filtration and supernatant was evaporated to dryness, co-evaporated with chloroform and dried under vacuum. The crude dye was then purified on Biotage SP4 system using a gradient of methanol in chloroform. Appropriate fractions were combined and evaporated to dryness to provide Compound 17 (1.0 g) as a red solid. Rf (9:1 CHCl3/MeOH): 0.46; Abs (max, PBS)=500 nm. The structure of Compound 17 is given below:

後処理

  1. temperatureheated in an oil bath (T=100° C.) for 45 minutes
  2. customReaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered
  5. additionTo the filtrate petroleum ether (50 mL) was added
  6. stirringwas stirred at 4° C. over night
  7. customPrecipitated solid
  8. customwas removed by filtration and supernatant
  9. customwas evaporated to dryness, co-evaporated with chloroform
  10. customdried under vacuum
  11. customThe crude dye was then purified on Biotage SP4 system
  12. customevaporated to dryness

出典と根拠

ORDレコード
ord-16fd1327c7c2454691174437859f1ca9
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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