1,4-Dibromobutane → 1-Benzhydryl-3-{[3-(4-bromobutoxy)phenyl]methanesulfonylmethylene}azetidine

HRID 1058842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058842
C(N1CC(=C([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:34])[CH:24]=2)S(C)(=O)=O)C1)(C1C=CC=CC=1)C1C=CC=CC=1.BrCCCCBr.C(=O)([O-])[O-].[K+].[K+].[CH:47]([N:60]1[CH2:63][C:62](=[C:64](C2C=CC=C(O)C=2)[S:65]([CH3:68])(=[O:67])=[O:66])[CH2:61]1)([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CC(CC)=O>[CH:47]([N:60]1[CH2:61][C:62](=[CH:64][S:65]([CH2:68][C:27]2[CH:28]=[CH:23][CH:24]=[C:25]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Br:34])[CH:26]=2)(=[O:67])=[O:66])[CH2:63]1)([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1

Komponenten

6

Edukt 4

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 225653671-Benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidineHCID 57042851HCID 57042851, Verbindung

Produkt 1

HCID 225652911-Benzhydryl-3-{[3-(4-bromobutoxy)phenyl]methanesulfonylmethylene}azetidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

1-Benzhydryl-3-{[3-(4-bromobutoxy)phenyl]-methanesulfonylmethylene}azetidine may be prepared in the following manner: 0.586 cm3 of 1,4-dibromobutane and 255 mg of potassium carbonate are successively added at a temperature close to 20° C., under an inert atmosphere of argon, to a solution of 500 mg of 1-benzhydryl-3-[(3-hydroxyphenyl)(methylsulfonyl)methylene]azetidine in 10 cm3 of methylethyl ketone. The reaction mixture is heated at the reflux temperature of the solvent, under an inert atomosphere of argon, for 7 hours and then left at a temperature close to 20° C. for about 4 days. The reaction mixtue is filtered on sintered glass covered with celite. The solid residue is rinsed with ethyl acetate and then the filtrate is concentrated to dryness under reduced pressure (10 kPa) at a temperature close to 40° C. The brown oil obtained is purified by chromatography at atmospheric pressure on 40 g of silica (0.063-0.200 mm) contained in a column 3 cm in diameter, eluting with a methanol-dichloromethane mixture (0.5-99.5 by volume). The fractions (10 cm3) containing only the desired product are combined and concentrated to dryness under reduced pressure (0.27 kPa) at 40° C. for 2 hours, 408.4 mg of 1-benzhydryl-3-{[3-(4-bromobutoxy)phenyl]methanesulfonylmethylene}azetidine are thus obtained in the form of a brown foam.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at the reflux temperature of the solvent, under an inert atomosphere of argon, for 7 hours
  2. waitleft at a temperature
  3. customclose to 20° C. for about 4 days
  4. filtrationThe reaction mixtue is filtered on sintered glass
  5. washThe solid residue is rinsed with ethyl acetate
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (10 kPa) at a temperature
  7. customclose to 40° C
  8. customThe brown oil obtained
  9. customis purified by chromatography at atmospheric pressure on 40 g of silica (0.063-0.200 mm)
  10. washeluting with a methanol-dichloromethane mixture (0.5-99.5 by volume)
  11. additionThe fractions (10 cm3) containing only the desired product
  12. concentrationconcentrated to dryness under reduced pressure (0.27 kPa) at 40° C. for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-a4e5e78f822a4322b535a84a8d261d80
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518264B2

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