1,3-Dibromopropane → HCID 61975301, Verbindung

HRID 526270

Reaktionsgleichung

Reaktionsgleichung von HRID 526270
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[Br:11][CH2:12][CH2:13][CH2:14]Br.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.BrCCCN(C)C1C=CC=CC=1>CN(C=O)C>[Br:11][CH2:12][CH2:13][CH2:14][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1

Komponenten

7

Edukt 5

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 84349N-Methyl-m-anisidineHCID 61288549N-(3-bromopropyl)-N-methylaniline

Produkt 1

HCID 61975301HCID 61975301, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

N-methyl-3-methoxyaniline (1.0 g, 7.294 mmol) was dissolved in anhydrous DMF (20 mL), to which 1,3-dibromopropane (1.48 mL, 14.589 mmol), K2CO3 (3.018 g, 21.884 mmol) and 18-crown-6 (0.24 g, 1.458 mmol) were added at room temperature, and reaction mixture stirred at 35° C. for 24 hours. The remaining procedure was followed as described for compound 14 to obtain compound 15. Yield: 0.760 g (75%). 1H NMR (500 MHz, CDCl3): δ 2.16 (tt, 2H, J=6.5, 13.5 Hz, Hc), 2.98 (s, 3H, NCH3, Ha), 3.46-3.54 (m, 4H, Hb and Hd), 3.83 (s, 3H, OMe), 6.32-6.66 (m, 2H, Hg and Hi), 6.38-6.42 (m, 1H, Ha), 7.16-7.21 (m, 1H, Hf); 13C NMR (125 MHz, CDCl3): δ 29.90 (Cc), 31.34 (Cd), 38.65 (Ca), 50.79 (Cb), 55.02 (OCH3), 98.77 (Ci), 101.26 (Ce), 105.31 (Cg), 129.81 (Cf), 150.32 (Cj), 160.72 (Ch). EI-MS: [M+H]+ C11H7BrNO calcd 258.05, obsd 258.04.

Aufarbeitung

  1. additionwere added at room temperature
  2. customreaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-c6fa1e697f8e44c7b02f6ea42e11034a
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345781B2

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