Potassium Iodide → 4-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine

HRID 875197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 875197
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8]([C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[N:9][OH:10])[S:4][N:3]=1.Cl.Cl[CH2:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1.[I-].[K+].N12CCCC1=NCCC2>C(#N)C>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[N:9][O:10][CH2:18][C:19]2[N:20]=[C:21]([NH2:24])[S:22][CH:23]=2)[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)[S:4][N:3]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 1363312531-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine

Produkt 1

HCID 866507364-[({[(3,4-Dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amineAusbeute 0,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred suspension of 1-(3,4-dichloro-1,2-thiazol-5-yl)-N-hydroxy-1-(3-thienyl)methanimine (1.60 g, 5.73 mmol), 4-(chloromethyl)-1,3-thiazol-2-amine hydrochloride (937 mg, 6.30 mmol) and potassium iodide (951 mg, 5.73 mmol) in acetonitrile (15 mL) at 0° C. was added 1,5-diazabicyclo(4.3.0)non-5-ene (1.44 mL, 12.0 mmol). The mixture was stirred 10 min at 0° C., then overnight at room temperature. After dilution of the reaction mixture with water and extraction with ethyl acetate, the combined organic layers were dried over MgSO4, concentrated in vacuo, and the residue purified by reverse phase HPLC to afford 4-[({[(3,4-dichloro-1,2-thiazol-5-yl)(3-thienyl)methylene]amino}oxy)methyl]-1,3-thiazol-2-amine [16 mg, yield 0.7%].

Aufarbeitung

  1. customovernight
  2. customat room temperature
  3. extractionAfter dilution of the reaction mixture with water and extraction with ethyl acetate
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customthe residue purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-00aa644909214e9a9a19f99d45f50abb
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08981111B2

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