Reacción #4312

Ecuación de reacción

2-(phenylsulfonyl)ethanamine

1,1'-carbonyldiimidazole

citric acid

N,N,N'-triethylethylenediamine

→

white crystalline solid

Rendimiento 52.0%

N-[2-(Diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea citrate

Rendimiento 52.0%

Disolventes

tetrahydrofuran

methanol

ether

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed for 16 hr
2. 2
   OtroThe solvent was removed in vacuo
3. 3
   Otrothe residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water
4. 4
   SecadoThe organic phase was dried over magnesium sulfate
5. 5
   Otrothe solvent was removed in vacuo
6. 6
   Otroto give an oil
7. 7
   workup.ADDITIONwas added
8. 8
   OtroA white precipitate formed

Procedimiento

A solution of 5.55 g (0.030 mole) of 2-(phenylsulfonyl)ethanamine and 5.35 g (0.033 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 4.62 g (0.032 mole) of N,N,N'-triethylethylenediamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water. The organic phase was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with an equivalent of citric acid and ether was added. A white precipitate formed to give 8.54 g (52.0%) of white crystalline solid, m.p. 105°-107° C.

Fuente