Réaction #1577

Équation de réaction

1-(5-acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea

pyridine

pyridine

N-(chlorocarbonyl) isocyanate

N-(chlorocarbonyl) isocyanate

→

title product

4'-Chloro-2'-fluoro-5'-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]acetanilide

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 90 minutes
2. 2
   Températurecooled to room temperature
3. 3
   workup.STIRRINGstirred for 10 minutes
4. 4
   Températurecooled to room temperature
5. 5
   Filtrationfiltered
6. 6
   Autreto obtain a solid
7. 7
   LavageThe solid is washed sequentially with water and hexanes
8. 8
   Autredried

Mode opératoire

A mixture of 1-(5-acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea (4.50 g, 15.9 mmol), and pyridine (2.56 mL, 31.8 mmol) in methylene chloride is treated with N-(chlorocarbonyl) isocyanate (1.92 mL, 23.9 mmol), stirred at room temperature overnight, refluxed for 90 minutes, cooled to room temperature, treated with additional pyridine (1.30 mL) and N-(chlorocarbonyl) isocyanate (1.92 mL), stirred for 10 minutes, cooled to room temperature, and filtered to obtain a solid. The solid is washed sequentially with water and hexanes, and dried to give the title product as a tan solid.

Source