Triethylamine → 4-bromo-N,N-dimethylbenzamide

HRID 1177130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177130
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][NH:13][CH3:14].C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:13]([CH3:14])[CH3:12])=[O:7])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 685154-Bromobenzoyl chloride

Produkt 1

HCID 1403894-bromo-N,N-dimethylbenzamideAusbeute 83,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-bromobenzoyl chloride (2.00 g, 9.11 mmol) and dimethyl amine hydrochloride (892 mg, 10.90 mmol) in 20 mL of CH2Cl2 was added triethylamine (3.81 mL, 27.30 mmol). The mixture was stirred at room temperature for 2 h, quenched with water, extracted with 3×CHCl3, dried with Na2SO4, concentrated and purified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2 to give a white solid (1.73 g, 83% yield). 1H NMR (400 MHz, CDCl3) δ 7.48-7.65 (m, 2 H) 7.20-7.37 (m, 2 H) 3.05 (d, J=50.78 Hz, 6 H); LCMS for C9H10BrNO m/z 228.00 and 230.00 (M+H)+

Aufarbeitung

  1. customquenched with water
  2. extractionextracted with 3×CHCl3
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by Biotage column chromatography with 1-4% MeOH in 1:1 EtOAc/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-dbe5a481fed240deb2d26db14fe096b8
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842713B2

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