4-Methylmorpholine → 2-(4'-Bromobiphenyl-4-yl)-N-methoxy-N-methylacetamide

HRID 1626788

Reaktionsgleichung

Reaktionsgleichung von HRID 1626788
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.[CH3:19][NH:20][O:21][CH3:22].[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1>O1CCCC1.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([N:20]([O:21][CH3:22])[CH3:19])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 13942454'-Bromo-4-carboxymethylbiphenylHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

Produkt 1

HCID 866700832-(4'-Bromobiphenyl-4-yl)-N-methoxy-N-methylacetamideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4′-Bromobiphenyl-4-yl)acetic acid (12 g, 37 mmol) was dissolved in a mixed solvent of tetrahydrofuran (200 mL) and methanol (200 mL), and N,O-dimethylhydroxylamine hydrochloride (5.4 g, 56 mmol), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (15 g, 60 mmol) and N-methylmorpholine (6.1 mL, 56 mmol) were added, followed by stirring at room temperature for 1 hour. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the resulting residue, and the organic layer was washed with water. After the solvent was distilled off under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (12 g, 37 mmol) as a white solid (yield 100%).

Aufarbeitung

  1. additionwere added
  2. concentrationAfter the reaction solution was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the resulting residue
  4. washthe organic layer was washed with water
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  7. concentrationa fraction corresponding to the Rf value=0.45 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2d614cf624984dca89529b848563f4ae
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785462B2

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