Benzylamine → HCID 178488570, Verbindung

HRID 493496Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 493496
[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[O-]S([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[CH2:18](/[N:25]=[CH:16]\[C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([Br:1])[CH:3]=2)=[CH:11][CH:12]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 576816103'-Bromo-4'-methoxy-1,1'-biphenyl-4-carbaldehyde

Produkt 1

HCID 178488570HCID 178488570, VerbindungAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3′-bromo-4′-methoxy-1,1′-biphenyl-4-carbaldehyde (19.4 g, 69 mmol), prepared in step 3 of Example 6, benzylamine (38 mL, 345 mmol) and 60 g of anhydrous MgSO4 in 400 mL of methylene chloride was stirred under nitrogen at room temperature for 18 h. The reaction was filtered and the filtrate concentrated under reduced pressure to give an off-white solid. The solid was triturated with hexane and dried under reduced pressure to give N-benzyl-N-[(1Z)-(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methylidene]amine (23.6 g, 88%) as an off-white solid, MS KESI) m/z 380 [M+H]+. Elemental analysis for C21H18BrNO: Calc'd: C, 66.33; H, 4.77; N, 3.68; Found: C, 63.22; H, 4.85; N, 4.17

Aufarbeitung

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto give an off-white solid
  4. customThe solid was triturated with hexane
  5. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5a526a0f595d4ea1a2feffe915905b36
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07534894B2

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