Reaktion #63159

Reaktionsgleichung

hydrochloric acid

product

2-[(2-oxotetrahydro-3-furanylidene)methyl] benzenesulfonamide

(4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester

1,8- diazabicyclo[5.4.0]undec-7-ene

→

title compound

Ausbeute 64.0%

N-[(4,6-Dimethoxypyrimidin-2-yl)-aminocarbonyl]-2-[(2-oxotetrahydro-3-furanylidene)methyl]benzenesulfonamide

Ausbeute 64.0%

Lösungsmittel

acetonitrile

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe resulting precipitate was collected by filtration
2. 2
   Waschenwashed well with water and ether

Vorschrift

To a stirred suspension of 0.09 g (0.0004 mol) of the product of Example 3 and 0.15 g (0.0005 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.08 mL (0.08 g, 0.0005 mol) of 1,8- diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room temperature for 30 min and was then diluted with water and acidified with 1N aqueous hydrochloric acid. The resulting precipitate was collected by filtration and washed well with water and ether to yield 0.1 g (64%) of the title compound: m.p. 185°-190° (gas evolution); IR (nujol) 3180 (br), 1755, 1740, 1710, 1700, 1610, 1560, 1355, 1165, cm-1 ; NMR (CDCl3, 200 MHz) δ 3.05 (2H, m), 4.29 (2H, t, J=7 Hz), 3.99 (6H, s), 5.83 (1H, s), 7.2 (NH, s), 7.4-7.8 (3H, m), 8.1 (1H, m), 8.12 (NH, s), 8.14 (1H, m).

Quelle