4-Methylmorpholine → 2-(4'-Bromobiphenyl-4-yl)-N,N-dimethylacetamide

HRID 1626793

Reaktionsgleichung

Reaktionsgleichung von HRID 1626793
[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][CH3:21].[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]([CH3:21])[CH3:19])=[O:17])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 10473Dimethylamine, hydrochlorideHCID 13942454'-Bromo-4-carboxymethylbiphenylHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride

Produkt 1

HCID 681932812-(4'-Bromobiphenyl-4-yl)-N,N-dimethylacetamideAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4′-Bromobiphenyl-4-yl)acetic acid (1.0 g, 3.4 mmol) was dissolved in a mixed solvent of tetrahydrofuran (20 mL) and methanol (20 mL), and dimethylamine hydrochloride (0.42 g, 5.2 mmol), 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (1.3 g, 4.7 mmol) and N-methylmorpholine (0.95 mL, 8.6 mmol) were added, followed by stirring at room temperature for 18 hours. After the reaction solution was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate), and a fraction corresponding to the Rf value=0.55 (dichloromethane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.82 g, 2.6 mmol) as a white solid (yield 75%).

Aufarbeitung

  1. additionwere added
  2. concentrationAfter the reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: dichloromethane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.55 (dichloromethane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-592cbb6cc2b04eb198e76dc0694769d9
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785462B2

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