Reaktion #80445

Reaktionsgleichung

N,O-Bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine

ammonium hydroxide

→

N-hydroxy-N-(3-butyn-2-yl)urea

Ausbeute 28.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   WaschenThe organic solution was washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated

Vorschrift

A mixture of N,O-Bis(phenoxycarbonyl)-N-(3-butyn-2-yl)hydroxylamine (3.14 g,9.7 mmol), methanol (20 mL), and ammonium hydroxide (20 mL) was stirred for 17 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate. The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated. Chromatography on silica gel (2% methanol, methylene chloride) afforded N-hydroxy-N-(3-butyn-2-yl)urea (340 mg, 28%). 1H NMR (DMSO-26, 300 MHz) δ1.25 (d, 3H, J=7.5 Hz), 3.05 (d, 1H, J=3.0 Hz), 4.85 (dq, 1H, J=7.5, 3.0 Hz), 6.50 (br s, 1H), 9.25 (s, 1H). MS (DCI/NH3) m/e 129 (M+H)+, 146 (M+NH4)+. Anal calcd for C5H8N2O2 : C, 46.87; H, 6.29; N, 21.86. Found: C, 47.03; H, 6.27; N, 21.98.

Quelle