Water → HCID 178485051, Verbindung

HRID 1059880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059880
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:21]([NH:23][C:24](=[N:27][CH3:28])SC)#[N:22].O>CN(C)C=O>[C:21]([N:23]=[C:24]([N:27]([CH3:28])[C:24]([NH:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)=[C:5]([CH3:7])[N:6]=1)=[N:23][C:21]#[N:22])[NH:27][CH3:28])#[N:22]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1111031-Cyano-2,3-dimethylisothioureaHCID 186309852-Amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole

Produkt 1

HCID 178485051HCID 178485051, VerbindungAusbeute 14,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a suspension of 2-amino-4-methyl-5-(4-methylpyridin-2-yl)-thiazole (308 mg) and potassium carbonate (207 mg) in N,N-dimethylformamide (5 ml) was added N-cyano-N′,S-dimethylisothiourea (194 mg), and the mixture was stirred at 100° C. for 12 hours. The mixture was poured into water and extracted with ethyl acetate-tetrahydrofuran (2:1, 150 ml×2). The organic layer was washed with brine and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 10 g, 0 to 2% methanol in dichloromethane) to give 2,4-dicyano-1,3-dimethyl-5-(4-methyl-5-(4-methylpyridin-2-yl)thiazol-2-yl)biguanide (41 mg) as a mixture of regioisomers.

Aufarbeitung

  1. extractionextracted with ethyl acetate-tetrahydrofuran (2:1, 150 ml×2)
  2. washThe organic layer was washed with brine
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (silica gel 10 g, 0 to 2% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-cbfbb6b805b54e07abf90b195cd8abb8
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521643B1

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