Acetyl chloride → HCID 21947396, Verbindung

HRID 2214642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2214642
Cl.[F:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[OH-].[Na+].[C:21](Cl)([CH3:23])=[O:22]>C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:21](=[O:22])[CH3:23])=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 21947523HCID 21947523, Verbindung

Produkt 1

HCID 21947396HCID 21947396, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Bis-(4-fluoro-benzyl)-amine hydrochloride (43 grams, 0.16 mole) was suspended in 200 mL of CH2Cl2. To this was added 730 mL of 1N NaOH. The reaction mixture was stirred vigorously while AcCl (20 mL, 0.28 mole) was slowly added. The reaction was stirred for 0.5 h, then the organic layer separated, washed with 1N HCl, dried over Na2SO4, filtered and the solvent removed under vacuum to yield 24 grams (55% yield) of N,N-bis-(4-fluoro-benzyl)-acetamide as an oil. MS (M+H) calcd for C16H16F2NO: 276.1. found: 276.0. Anal. calcd for C16H15F2NO: C, 69.80; H, 5.49; N, 5.08. found: C, 69.53; H, 5.41; N, 5.06. 1H NMR (500 MHz, DMSO) δ: 2.10 (s, 3), 4.45 (s, 2), 4.50 (s, 2), 7.11–7.27 (overlapping m, 8). 13C NMR (125 MHz, DMSO) δ: 21.34, 50.04, 54.80, 114.90, 115.07, 115.27, 115.45, 128.51, 128.58, 129.57, 129.64, 133.32, 133.34, 133.86, 133.89, 160.25, 160.33, 162.27, 170.22.

Aufarbeitung

  1. additionwas slowly added
  2. customthe organic layer separated
  3. washwashed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5bcc1c4bd1664318859396c3c008cbb0
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109186B2

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