Epichlorohydrin → 3-Chloro-9-(oxiran-2-ylmethyl)carbazole

HRID 2111495

Reaktionsgleichung

Reaktionsgleichung von HRID 2111495
[OH-].[K+].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[NH:15][C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3.[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl>>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:24][CH:26]3[O:28][CH2:27]3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3

Komponenten

5

Edukt 4

HCID 7835EpichlorohydrinHCID 14797Potassium Hydroxide4×HCID 24436Sodium Sulfate4×HCID 5203023-Chlorocarbazole2×

Produkt 1

HCID 43418103-Chloro-9-(oxiran-2-ylmethyl)carbazole

Versuchsvorschrift

Compound (3) may be prepared according to the following procedure. A mixture of potassium hydroxide powder (KOH, 85%, 198 g, 3 mol) and anhydrous sodium sulfate (Na2SO4, 51 g, 0.369 mol) is added in three stages to a mixture of 3-chloro-9H-carbazole (1 mol) and epichlorohydrin (1.5 mol), while keeping the reaction mixture at 20-25° C. The 3 stage quantities added are 33 g of Na2SO4 and 66 g of KOH initially; 9.9 g of Na2SO4 and 66 g of KOH after 1 hour of reaction; and 9.9 g of Na2SO4 and 66 g of KOH after 2 hours of reaction. The reaction mixture is stirred vigorously at 35-40° C. until 3-chloro-9H-carbazole disappears (approximately 3-4 hours). Subsequently, the mixture is cooled to room temperature, and any remaining solids are removed by filtration. The liquid organic phase is treated with a solvent such as diethyl ether and washed with distilled water until the washed water reaches a neutral pH. The organic layer is dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered. The solvent and excess epichlorohydrin are removed by evaporation in a rotory evaporator. The residue is purified by recrystallization, chromatography, or a combination of both to produce 3-chloro-9-(2,3-epoxypropyl)carbazole.

Aufarbeitung

  1. customat 20-25° C
  2. additionThe 3 stage quantities added
  3. custom(approximately 3-4 hours)
  4. customany remaining solids are removed by filtration
  5. additionThe liquid organic phase is treated with a solvent such as diethyl ether
  6. washwashed with distilled water until the washed water
  7. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  8. additiontreated with activated charcoal
  9. filtrationfiltered
  10. customThe solvent and excess epichlorohydrin are removed by evaporation in a rotory evaporator
  11. customThe residue is purified by recrystallization, chromatography

Quellen und Nachweise

ORD-Eintrag
ord-54192d6a6539407385eafa069b776c20
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521162B2

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