Triethylamine → Triethylammonium bromide

HRID 536221

Reaktionsgleichung

[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=1[NH2:8].[CH3:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19].N#C[Br:24]>C(Cl)Cl>[CH3:14][O:13][C:9]1[C:7]2[N:8]=[C:16]([NH2:17])[N:3]3[CH2:4][CH2:5][N:1]=[C:2]3[C:6]=2[CH:12]=[CH:11][CH:10]=1.[N:17]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:15].[BrH:24]

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

2-(4,5-Dihydro-1H-imidazol-2-yl)-6-methoxyaniline (Step 3, 22.0 g, 115 mmol) and Et3N (48.1 mL, 345 mmol) were dissolved in CH2Cl2 (200 mL), cooled to 10° C. in an ice bath and cyanogen bromide (24.4 g, 230 mmol) was added portionwise. A slight exotherm was noted, and the reaction was stirred overnight. The reaction was concentrated under reduced pressure, then treated with EtOAc (150 mL) and concentrated under reduced pressure again. Finally, the residue was treated with Heptane and concentrated under reduced pressure to give the title compound as a mixture with Et3N.HBr (62 g, 99%): HPLC MS RT=1.08 min, MH+=217.1; 1H NMR (DMSO-d6+2 drops TFA-d) δ: 3.85 (3H, s), 4.09-4.16 (2H, m), 4.31-4.38 (2H, m), 7.23 (1H, t), 7.31 (1H, d), 7.57 (1H, dd).

Aufarbeitung

concentrationThe reaction was concentrated under reduced pressure
additiontreated with EtOAc (150 mL)
concentrationconcentrated under reduced pressure again
additionFinally, the residue was treated with Heptane
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-cbf1799c49494e7eaaac2cf948a53bb4
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08859572B2

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