Réaction #63160

Équation de réaction

hydrochloric acid

product

3-Chloro-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

Rendement 85.3%

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

Rendement 85.3%

Solvants

acetonitrile

water

Conditions de réaction

Traitement

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

Mode opératoire

To a stirred suspension of 0.15 g (0.0005 mol) of the product of Example 7 and 0.21 g (0.0008 mol) of (4,6-dimethoxy-2-pyrimidinyl)carbamic acid, phenyl ester in 1 mL dry acetonitrile under nitrogen was added dropwise 0.12 mL (0.12 g, 0.0008 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture was stirred at room temperature for 1 hour 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 0.2 g (83%) of the title compound: m.p. 212°-216° (dec); IR (nujol) 3410, 1765, 1605, 1365, 1340, 1155 cm-1 ; NMR (CDCl3, 200 MHz) δ 2.7-2.8 (2H, m), 3.94 (6H, s), 4.1-4.2 (2H, m), 5.84 (1H, s), 7.2-7.8 (3H, m), 8.25 (1H, m).

Source