Triethylamine → 4-[6-(1-Amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochloride

HRID 1491862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1491862
[ClH:1].Cl.Cl.[NH2:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[NH2:28][C:29]1[C:32](=[O:33])[C:31](=[O:34])[C:30]=1OCC>CO>[ClH:1].[NH2:28][C:29]1[C:32](=[O:33])[C:31](=[O:34])[C:30]=1[NH:4][CH2:5][C:6]1[N:11]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 151463363-Amino-4-ethoxycyclobut-3-ene-1,2-dioneHCID 189538374-(6-Aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride

Produkt 1

HCID 189538944-[6-(1-Amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochlorideAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 4-(6-aminomethylpyridin-2-yl)-2-(diaminomethyleneamino)thiazole trihydrochloride (1.5 g), triethylamine (1.8 ml) and 1-amino-2-ethoxy-1-cyclobutene-3,4-dione (0.65 g) in methanol (30 ml) was heated under reflux for 7 hours. The solvent was removed by concentration in vacuo. To the residue was added a mixture of water and ethyl acetate, and the mixture was adjusted to pH 1.0 with 6N-hydrochloric acid. The isolated precipitate was collected by filtration and dried. The precipitate was recrystallized from an aqueous N,N-dimethylformamide to give 4-[6-(1-amino-3,4-dioxo-1-cyclobuten-2-yl)aminomethylpyridin-2-yl]-2-(diaminomethyleneamino)thiazole hydrochloride (1.17 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customThe solvent was removed by concentration in vacuo
  4. additionTo the residue was added
  5. additiona mixture of water and ethyl acetate
  6. filtrationThe isolated precipitate was collected by filtration
  7. customdried
  8. customThe precipitate was recrystallized from an aqueous N,N-dimethylformamide

Quellen und Nachweise

ORD-Eintrag
ord-f6824f9f12ef4d0db0995a9b7652a932
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371097

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