Dichloromethane → N-Hydroxy-1-methoxycyclopropanecarboximidamide

Temperatur

60 °C

100 mg (1.03 mmol) of 1-methoxycyclopropanecarboxamide [L. N. Owen, H. M. Babatunde Somade, J. Chem. Soc. 1947, 1030-1034] in tetrahydrofuran (22.7 ml) was admixed with 1.51 g (6.08 mmol) of methyl N-(triethylammoniumsulphonyl)carbamate (Burgess reagent) and then stirred at 60° C. for 1.5 h. The reaction mixture was admixed with dichloromethane and water, and the organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure (637 mg of crude product). 100 mg of the crude product were initially charged in ethanol (1.2 ml), admixed with 107 mg (1.55 mmol) of hydroxylammonium chloride and 0.17 ml (125 mg, 1.24 mg) of triethylamine and then stirred under reflux overnight. The reaction solution was concentrated under reduced pressure, and the residue was admixed with saturated aqueous sodium chloride solution and then extracted with dichloromethane. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was subsequently stirred with ethyl acetate, the insoluble salts were filtered off and the filtrate was concentrated under reduced pressure. Yield: 32.3 mg (23% of theory)

1. dry with materialthe organic phase was dried over magnesium sulphate
2. filtrationfiltered
3. concentrationconcentrated under reduced pressure (637 mg of crude product)
4. addition100 mg of the crude product were initially charged in ethanol (1.2 ml)
5. stirringstirred
6. temperatureunder reflux overnight
7. concentrationThe reaction solution was concentrated under reduced pressure
8. extractionextracted with dichloromethane
9. dry with materialThe organic phase was dried over magnesium sulphate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. stirringThe residue was subsequently stirred with ethyl acetate
13. filtrationthe insoluble salts were filtered off
14. concentrationthe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-50c0f207c84d48878b9b6b00b06dc05c

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08202862B2