Epichlorohydrin → 4-(3-chloro-2-hydroxypropylamino)-N-methylphthalimide

HRID 223598

Reaktionsgleichung

Reaktionsgleichung von HRID 223598
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[CH:12][CH:13]=1.[Cl:14][CH2:15][CH:16]1[O:18][CH2:17]1>FC(F)(F)CO>[Cl:14][CH2:15][CH:16]([OH:18])[CH2:17][NH:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[CH:12][CH:13]=1

Komponenten

4

Edukt 2

HCID 7835EpichlorohydrinHCID 7269315-amino-2-methyl-2,3-dihydro-1H-isoindole-1,3-dione

Produkt 1

HCID 212817364-(3-chloro-2-hydroxypropylamino)-N-methylphthalimideAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64092,2,2-TrifluoroethanolLösungsmittel

Versuchsvorschrift

Twenty-five grams (g) (0.142 mole) 4-amino-N-methylphthalimide [Flitsch, Chem. Ber. 94:2494(1961)] and 20.7 g (0.21 mole) 1-chloro-2,3-epoxypropane were added to 150 ml 2,2,2-trifluoroethanol and the reaction mixture was heated to reflux with stirring for 48 hours. Seventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation and a heavy yellow precipitate formed when the remaining solution cooled to room temperature. This precipitate was triturated with ethyl acetate, collected by filtration and dried to give 29.5 g (77% yield) of the desired phthalimide intermediate m.p. 136°-138.5° C.

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux
  3. customSeventy to eighty ml of 2,2,2-trifluoroethanol was removed by distillation
  4. customa heavy yellow precipitate formed when the remaining solution
  5. customThis precipitate was triturated with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4d2f82aacd4b40b9b3cb8c568cd4c23a
Quelldatensatz
uspto-grants-1982_10
Patentnummer
US04355165

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