Water → 2-[2-(1-Azetidinyl)ethyl]-7-chloro-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one oxalate

HRID 1193859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1193859
[Cl:1][C:2]1[C:12]([CH3:13])=[N:11][C:10]2[O:9][CH:8]([CH2:14][CH2:15]Cl)[CH2:7][N:6]([CH3:17])[C:5](=[O:18])[C:4]=2[CH:3]=1.[C:19](=[O:22])([O-:21])[O-].[Na+].[Na+].[NH:25]1[CH2:28][CH2:27][CH2:26]1.[OH2:29]>CS(C)=O>[C:5]([OH:18])(=[O:29])[C:19]([OH:21])=[O:22].[N:25]1([CH2:15][CH2:14][CH:8]2[CH2:7][N:6]([CH3:17])[C:5](=[O:18])[C:4]3[CH:3]=[C:2]([Cl:1])[C:12]([CH3:13])=[N:11][C:10]=3[O:9]2)[CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10422AzetidineHCID 143915077-Chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one

Produkt 1

HCID 212725992-[2-(1-Azetidinyl)ethyl]-7-chloro-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one oxalate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 5.0 g (0.017 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4,8-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one in 20 ml of dimethyl sulfoxide was added ~7 g of sodium carbonate (crushed) and 2.46 g (0.043 mole) of azetidine. The reaction mixture was stirred for 2 days at room temperature and poured into 200 ml of water. The aqueous mixture was extracted with 3×100 ml of benzene. The combined benzene extracts were washed with 2×100 ml of water, dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residue was treated with oxalic acid in isopropyl alcohol which gave 5 g (73%) of white analytically pure crystals, m.p. 191°-92° C.

Aufarbeitung

  1. extractionThe aqueous mixture was extracted with 3×100 ml of benzene
  2. washThe combined benzene extracts were washed with 2×100 ml of water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. additionThe residue was treated with oxalic acid in isopropyl alcohol which
  7. customgave 5 g (73%) of white analytically pure crystals, m.p. 191°-92° C.

Quellen und Nachweise

ORD-Eintrag
ord-2444f247ee16492381dbcbcf56e2addf
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810795

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