Potassium Carbonate → (2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N-hydroxy-2-(3-methoxyphenyl)-N-methylethanimidamide

HRID 520251

Reaktionsgleichung

Reaktionsgleichung von HRID 520251
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:13]2[CH:18]=[CH:17]C=C(OC)C=2)\[C:11]#[N:12])[N:6]=1.[C:21](=O)([O-])[O-].[K+].[K+].Cl.[CH3:28][NH:29][OH:30].[CH3:31][CH:32]([OH:34])[CH3:33].O>>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8]/[N:9]=[C:10](/[C:13]2[CH:18]=[CH:17][CH:33]=[C:32]([O:34][CH3:21])[CH:31]=2)\[C:11](=[NH:12])[N:29]([OH:30])[CH3:28])[N:6]=1

Komponenten

5

Edukt 4

HCID 11430Potassium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 21889133Propan-2-ol--water (1/1)HCID 89655523(1Z)-N-[(2-amino-1,3-thiazol-4-yl)methoxy]-3-methoxybenzenecarboximidoyl cyanide

Produkt 1

HCID 89656222(2Z)-2-[(2-amino-1,3-thiazol-4-yl)methoxyimino]-N-hydroxy-2-(3-methoxyphenyl)-N-methylethanimidamideAusbeute 69 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile (4.00 g, 13.87 mmol, 1 eq.) in 2-propanol/water (60 ml/16 ml), was added potassium carbonate (3.84 g, 27.75 mmol, 2.0 eq) and N-methylhydroxylamine hydrochloride (2.32 g, 27.75 mmol, 2 eq.). The reaction was heated under stirring to 80° C. for 2 h. The residue was extracted with EtOAc and washed with water. The organics were combined, dried over MgSO4 and concentrated to give (2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-(3-methoxyphenyl)ethanimidamide (3.36, 69% yield), as a yellow solid.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. extractionThe residue was extracted with EtOAc
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e75c7053610b480ab70838b0eda414b4
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09326515B2

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