Methylamine → HCID 178485037, Verbindung

HRID 1033050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1033050
[NH2:1][CH2:2][C:3]1[O:7][C:6]([C:8]2[N:9]=[C:10]([N:13]=[C:14]([NH2:16])[NH2:15])[S:11][CH:12]=2)=[CH:5][CH:4]=1.CS[C:19](SC)=[N:20][C:21]#[N:22].[CH3:25][NH2:26]>CN(C)C=O>[NH2:15][C:14](=[N:13][C:10]1[S:11][CH:12]=[C:8]([C:6]2[O:7][C:3]([CH2:2][NH:1][C:19]([NH:26][CH3:25])=[N:20][C:21]#[N:22])=[CH:4][CH:5]=2)[N:9]=1)[NH2:16]

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 103992684-(5-Aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole

Produkt 1

HCID 178485037HCID 178485037, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (7.00 g) and dimethyl N-cyanodithioiminocarbonate (4.31 g) in N,N-dimethylformamide (70 ml) was stirred at 70° C. for two hours. 40% Aqueous methylamine by weight (14 ml) was added to the warmed solution and the mixture was stirred for an additional one hour at the same temperature. After the solvent was evaporated in vacuo, the residue was chromatographed on alumina, eluting with a mixture of chloroform and methanol (9:1, V/V), followed by recrystallization from a mixture of methanol, tetrahydrofuran and diisopropyl ether to afford 2-(diaminomethyleneamino)-4-[5-(2-cyano-3-methylguanidino)methylfuran-2-yl]thiazole (4.05 g).

Aufarbeitung

  1. customAfter the solvent was evaporated in vacuo
  2. customthe residue was chromatographed on alumina
  3. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  4. customfollowed by recrystallization from a mixture of methanol, tetrahydrofuran and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d16879bb2bd54dc0a052fd66b7be1ec5
Quelldatensatz
uspto-grants-1994_05
Patentnummer
US05308857

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