Propylene Oxide → HCID 12952416, Verbindung

HRID 1390920

Reaktionsgleichung

Reaktionsgleichung von HRID 1390920
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9]Br)=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13].[CH3:16][CH:17]([NH:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1OC1C>CC(=O)CC>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:11])[CH2:9][N:26]([CH:17]([CH3:16])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:4][C:3]=1[S:12]([NH2:15])(=[O:14])=[O:13]

Komponenten

5

Edukt 3

HCID 6378Propylene OxideHCID 4362644N-benzyl-4-phenylbutan-2-amineHCID 12952403HCID 12952403, Verbindung

Produkt 1

HCID 12952416HCID 12952416, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A solution of 2-amino-5-(2-bromoacetyl)benzenesulphonamide (0.5 g), N-(1-methyl-3-phenylpropyl)-N-(phenylmethyl) amine (0.45 g) and propylene oxide (2.5 ml) in 2-butanone (30 ml) was heated under reflux for 3 hours. The solution was then concentrated to a red-brown oil (0.7 g) which was dissolved in absolute ethanol (30 ml) and treated with sodium borohydride (258 mg) at room temperature during 2 hours. Excess borohydride was then destroyed with 2N hydrochloric acid and the ethanol was removed under reduced pressure. The residue was basified with 8% sodium bicarbonate and extracted with ethyl acetate (3 × 50 ml). The extracts were washed with water (100 ml), dried and concentrated to an orange oil (0.63 g). The oil was dissolved in acetone (10 ml) and re-precipitated as an orange solid (340 mg) by addition of petroleum ether (b.p. 60°-80°). Chromatographic purification of this solid on silica plates [Merck St17; elution with chloroform: methanol (5:1 )] and conversion of the product into a hydrochloride salt gave the title compound, 0.2 g, m.p. 133°-136°.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. concentrationThe solution was then concentrated to a red-brown oil (0.7 g) which
  3. dissolutionwas dissolved in absolute ethanol (30 ml)
  4. additiontreated with sodium borohydride (258 mg) at room temperature during 2 hours
  5. customExcess borohydride was then destroyed with 2N hydrochloric acid
  6. customthe ethanol was removed under reduced pressure
  7. extractionextracted with ethyl acetate (3 × 50 ml)
  8. washThe extracts were washed with water (100 ml)
  9. customdried
  10. concentrationconcentrated to an orange oil (0.63 g)
  11. dissolutionThe oil was dissolved in acetone (10 ml)
  12. customre-precipitated as an orange solid (340 mg) by addition of petroleum ether (b.p. 60°-80°)
  13. customChromatographic purification of this solid
  14. washon silica plates [Merck St17; elution with chloroform: methanol (5:1 )] and conversion of the product into a hydrochloride salt

Quellen und Nachweise

ORD-Eintrag
ord-2309abf70acc471fb65385e09488ab8f
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140713

Verknüpfte Notizen

Wird geladen…