Methanol → 5,10-Bis(2-hydroxypropyl)-5,10-dihydrophenazine

HRID 413610

反応式

HRID 413610 の反応式
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([N:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[Na].[CH2:16]1[O:19][CH:17]1[CH3:18].[CH3:20]O.C(OCC[O:27][CH2:28][CH3:29])C>>[OH:19][CH:17]([CH3:16])[CH2:18][N:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[N:13]([CH2:20][CH:28]([OH:27])[CH3:29])[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]1=2

参加物

6

反応物 5

HCID 887MethanolHCID 4757PhenazineHCID 6378Propylene OxideHCID 12375Ethylene glycol diethyl ether2 回HCID 5360545Sodium

生成物 1

HCID 185208435,10-Bis(2-hydroxypropyl)-5,10-dihydrophenazine

反応条件

温度
120 °C

実験手順

40 g (0.22 mol) of phenazine are dissolved in 500 ml of anhydrous 1,2-diethoxyethane at 80° C. under an argon atmosphere. 14 g of sodium are added. The reaction mixture is stirred vigorously under reflux at 120° C. for 24 hours and cooled to room temperature. A solution of 39 g (0.66 mol) of 1,2-propylene oxide in 50 ml of 1,2-diethoxyethane is poured into the resultant 5,10-disodium 5,10-dihydrophenazine suspension. After the reaction mixture has been stirred at room temperature for 1 hour and at 50° C. for 2 hours, the precipitate is removed by filtration. All the anhydrous 1,2-diethoxyethane is distilled off on a rotary evaporator and used for the further synthesis. The solid residue, together with filtered-off precipitate, is mixed with 500 ml of methanol, and the mixture is stirred for 30 minutes. The solution is then evaporated on a rotary evaporator and transferred into a separating funnel, chloroform is added, and the mixture is washed a number of times with water and dried using magnesium sulphate. After the solvent has been distilled off, the product is purified by chromatography (silica gel column; cyclohexane/dioxane=1/1) and recrystallized from 150 ml of an acetone/water (2/1) mixture. The yield of the pale-green crystals is 22.5 g.

後処理

  1. temperaturecooled to room temperature
  2. stirringAfter the reaction mixture has been stirred at room temperature for 1 hour and at 50° C. for 2 hours
  3. customthe precipitate is removed by filtration
  4. distillationAll the anhydrous 1,2-diethoxyethane is distilled off on a rotary evaporator
  5. customused for the further synthesis
  6. stirringthe mixture is stirred for 30 minutes
  7. customThe solution is then evaporated on a rotary evaporator
  8. customtransferred into a separating funnel
  9. additionchloroform is added
  10. washthe mixture is washed a number of times with water
  11. customdried
  12. distillationAfter the solvent has been distilled off
  13. customthe product is purified by chromatography (silica gel column; cyclohexane/dioxane=1/1)
  14. customrecrystallized from 150 ml of an acetone/water (2/1) mixture

出典と根拠

ORDレコード
ord-d148991165cd4152b462abd82e05cf84
出典データセット
uspto-grants-2003_05
特許番号
US06569361B1

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