Triethylamine → 2-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-one

HRID 713399

Reaktionsgleichung

Reaktionsgleichung von HRID 713399
CCO[C:4]([CH:6]1[C:11](=O)[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].Cl.[Cl:14][CH2:15][C:16]([NH2:18])=[NH:17].C(N(CC)CC)C>CO>[Cl:14][CH2:15][C:16]1[NH:18][C:4](=[O:5])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:17]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 27769572-Chloroacetamidine monohydrochloride

Produkt 1

HCID 1354490022-(chloromethyl)-5,6,7,8-tetrahydroquinazolin-4(3H)-oneAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-cyclohexanone-carboxylate (5.5 g, 32 mmol) in methanol was added chloroacetamidine hydrochloride (4.2 g, 32 mmol) and triethylamine (14 mL, 97 mmol). The mixture was stirred at ambient temperature for 60 h. It was then concentrated under reduced pressure and purified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0) to provide product (0.82 g, 13% yield). 1H NMR (400 MHz, CD3OD) δ 4.40 (s, 2H), 2.61 (t, J=6.3 Hz, 2H), 2.45 (t, J=6.3 Hz, 2H), 1.68-1.87 (m, 4H). MS m/z 199.2 (M+1), retention time=0.94 min.

Aufarbeitung

  1. concentrationIt was then concentrated under reduced pressure
  2. custompurified via flash column chromatography (ethyl acetate:hexane, 10:90 to 100:0)

Quellen und Nachweise

ORD-Eintrag
ord-15e0a2eb507c40eba1e3825117b3276c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181266B2

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