m-ethylphenyl-N-methylcyanamide → HCID 178436385, Verbindung

HRID 257668

Reaktionsgleichung

Reaktionsgleichung von HRID 257668
[CH2:1]([C:3]1[CH:4]=[C:5]([N:9]([CH3:12])[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].[ClH:13].[F:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[NH2:25])=[CH:17][CH:16]=1>ClCCl>[ClH:13].[F:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[NH:25][C:10]([N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)[CH3:12])=[NH:11])=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 10103434m-ethylphenyl-N-methylcyanamideHCID 21191508HCID 21191508, Verbindung

Produkt 1

HCID 178436385HCID 178436385, VerbindungAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of N-(m-ethylphenyl)-N-methylcyanamide (195 mg, 1.21 mmol) and 7-fluoro-1-aminonaphthalene hydrochloride (200 mg, 1.01 mmol) was heated in a preheated oil bath at 160° C. for 2.5 hours and then allowed to cool to room temperature. The resulting solid was taken up in dichloromethane and washed with 5% NAOH solution. The organic layer was concentrated and the resulting residue was treated at room temperature with 0.5M methanol-HCl solution (10 ml). It was concentrated and the resulting purple glass was purified by flash chromatography on silica gel to give N-(7-fluoro-1-naphthyl)-N'-(m-ethylphenyl)-N'-methylguanidine hydrochloride (192 mg, 53%) as off-white crystals. M.p.: 187°-90° C. IR (CHCl3): 1630, 3400 cm-1. 1H NMR (CD3Cl3): δ 1.259 (t, 3H, J=7.9 Hz), 2.431 (q, 2H, J=7.9 Hz), 3.564 (s, 3H), 6.76-7.94 (m, 10H). Anal. Calcd for C20H21N3FCl: C, 67.12; H, 5.92; N, 11.74. Found: C, 67.28; H, 6.00; N, 11.87.

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed with 5% NAOH solution
  3. concentrationThe organic layer was concentrated
  4. additionthe resulting residue was treated at room temperature with 0.5M methanol-HCl solution (10 ml)
  5. concentrationIt was concentrated
  6. customthe resulting purple glass was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6005ab0495d743a680a8ba8a303a05b7
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05262568

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