4-Methylmorpholine → (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

HRID 2053752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053752
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=N1.CN1CCOCC1.N1CC=CC1>CN(C)C=O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[CH3:11])=[O:8])[CH2:20][CH:25]=[CH:24][CH2:23]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 660593-PyrrolineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Produkt 1

HCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).

Aufarbeitung

  1. additionThen it is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-13068a93f2ec4ec2ac10d0c3f94f8be7
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326791B2

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