Sodium Hydroxide → 2-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile

HRID 390328Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 390328
[C:1]1([C:7](=[N:14][CH2:15][C:16]#[N:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[C:1]1([C:7](=[N:14][CH:15]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[C:16]#[N:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 612957[(Diphenylmethylene)amino]acetonitrile

Produkt 1

HCID 584589102-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrileAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(diphenylmethyleneamino)acetonitrile (1.21 g, 5.47 mmol, 1.0 equiv) in CH2Cl2 (9.12 mL) was added 4-fluorobenzyl bromide (0.75 mL, 6.02 mmol, 1.1 equiv), benzyltrimethylammonium chloride (0.10 g, 0.547 mmol, 0.1 equiv), and NaOH (0.99 mL of a 10 M aqueous solution, 9.85 mmol, 1.8 equiv). The reaction was stirred vigorously for 18 h, at which time TLC analysis indicated complete consumption of the starting nitrile. The reaction was added to water and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane) to provide the title compound (1.65 g, 92% yield) as a viscous yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.65 (m, 2H), 7.38-7.48 (m, 4H), 7.31-7.38 (m, 2H), 7.00-7.09 (m, 2H), 6.89-6.97 (m, 2H), 6.84 (d, J=6.30 Hz, 2H), 4.35 (dd, J=7.81, 6.04 Hz, 1H), 3.10-3.29 (m, 2H); LCMS (ES+, (M+H)+) m/z 329.25.

Aufarbeitung

  1. customconsumption of the starting nitrile
  2. additionThe reaction was added to water
  3. extractionextracted with CH2Cl2 (×3)
  4. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bcd505dce2a9457487636a9990a7264e
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383639B2

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