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Dimethyl Sulfoxide → 2-[2-(1-Azetidinyl)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarate

HRID 4861
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 4861
Cl[CH2:2][CH2:3][CH:4]1[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]2[CH:13]=[CH:14][CH:15]=[N:16][C:6]=2[O:5]1.[C:17](=[O:20])([O-:19])[O-].[K+].[K+].[NH:23]1[CH2:26][CH2:25][CH2:24]1.CS(C)=[O:29]>>[C:6]([OH:29])(=[O:5])/[CH:7]=[CH:13]/[C:17]([OH:19])=[O:20].[N:23]1([CH2:2][CH2:3][CH:4]2[CH2:10][N:9]([CH3:11])[C:8](=[S:12])[C:7]3[CH:13]=[CH:14][CH:15]=[N:16][C:6]=3[O:5]2)[CH2:26][CH2:25][CH2:24]1
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Komponenten

5

Edukt 4

HCID 679Dimethyl SulfoxideHCID 10422Azetidine3×HCID 11430Potassium CarbonateHCID 137264422-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)thione

Produkt 1

HCID 137265622-[2-(1-Azetidinyl)ethyl]-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-thione fumarateAusbeute 31 %

Versuchsvorschrift

To 5.0 g (0.0914 mole) of 2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione dissolved in 50 ml of dimethylsulfoxide was added 8.04 g (0.058 mole) of potassium carbonate and 1.21 g (0.021 mole) of azetidine. The reaction mixture was stirred at room temperature for 8 hr after which was added 0.5 g (0.009 mole) of azetidine and the mixture was stirred overnight at room temperature. An additional 0.3 g (0.005 mole of azetidine was added and stirring was continued for 24 hr. The mixture was filtered and solvent removed by rotary evaporator at 80° C., 0.5 mm Hg. The residue was taken up in 100 ml of chloroform and the solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The residue was reacted with fumaric acid in isopropyl alcohol to give 2.5 g (31%) of pale yellow crystals, m.p. 122°-126° C.

Aufarbeitung

  1. stirringthe mixture was stirred overnight at room temperature
  2. stirringstirring
  3. waitwas continued for 24 hr
  4. filtrationThe mixture was filtered
  5. customsolvent removed by rotary evaporator at 80° C.
  6. washthe solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated by rotary evaporator
  10. customThe residue was reacted with fumaric acid in isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-cad802f8607b497e826f6484b8b5dd8e
Quelldatensatz
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04727152

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