1,1,3,3-Tetramethylguanidine → HCID 178467224, Verbindung

HRID 638218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 638218
Br[C:2](=[CH:6]OCC)[C:3](=[O:5])[CH3:4].Cl.[OH:11][CH2:12][C:13]([NH2:15])=[NH:14].CN(C)C(N(C)C)=N>CC(C)=O>[OH:11][CH2:12][C:13]1[NH:14][CH:6]=[C:2]([C:3](=[O:5])[CH3:4])[N:15]=1

Komponenten

5

Edukt 3

HCID 664601,1,3,3-TetramethylguanidineHCID 122173662-Hydroxy-acetamidine hydrochlorideHCID 534237433-Bromo-4-ethoxybut-3-EN-2-one

Produkt 1

HCID 178467224HCID 178467224, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

9.7 g (0.05 mole) of 3-bromo-4-ethoxy-3-buten-2-one was combined with 5.53 (0.05 mole) of hydroxyacetamidine hydrochloride in 100 ml acetone to form a slurry. To the slurry at 25° C. was added 11.5 g (0.1 mole) of 1,1,3,3-tetramethylguanidine over a period of 5 minutes. After stirring for 48 hours the slurry was filtered and the mother liquors were concentrated in vacuo to an oil which was chromatographed on silica gel 60 (E. Merck) using chloroform as eluent to give 1.48 g (21%) of 2-hydroxymethyl-4-acetylimidazole, m.p. 147°-148° C. 1H-NMR(DMSO-d6)ppm(delta): 7.73 (s, 1H), 5.46 (very broad s, 1H), 4.5 (broad s, 2H), 2.4 (s, 3H).

Aufarbeitung

  1. customto form a slurry
  2. filtrationwas filtered
  3. concentrationthe mother liquors were concentrated in vacuo to an oil which
  4. customwas chromatographed on silica gel 60 (E. Merck)

Quellen und Nachweise

ORD-Eintrag
ord-3f27b471bf8346c5b6954c4488b46dc9
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560690

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