Реакция #607433

ord-e75c7053610b480ab70838b0eda414b4

Уравнение реакции

COc1cccc(/C(C#N)=N/OCc2csc(N)n2)c1
(2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(3-methoxyphenyl)acetonitrile
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CNO.Cl
N-methylhydroxylamine hydrochloride
CC(C)O.O
2-propanol water
COc1cccc(/C(=N/OCc2csc(N)n2)C(=N)N(C)O)c1
(2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N-hydroxy-N-methyl-2-(3-methoxyphenyl)ethanimidamide
Выход 69.0%

Условия реакции

Температура
80°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураThe reaction was heated
  2. 2
    ЭкстракцияThe residue was extracted with EtOAc
  3. 3
    Промывкаwashed with water
  4. 4
    Сушкаdried over MgSO4
  5. 5
    Концентрированиеconcentrated

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09326515B2uspto-grants-2016_05