Réaction #4323

Équation de réaction

N,N-diethylethylenediamine

1,1'-carbonyldiimidazole

N-(2-propyl)-1-(phenylsulfonyl)-2-propanamine

→

N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[1-methyl-2-(phenylsulfonyl)ethyl]urea hydrate

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurethe solution was refluxed overnight
2. 2
   AutreThe solvent was removed in vacuo
3. 3
   Autrethe residue was partitioned between ether and water
4. 4
   SéchageThe ether solution was dried over magnesium sulfate
5. 5
   Autrethe solvent was removed in vacuo
6. 6
   Autreto give an oil
7. 7
   Autrechromatographed
8. 8
   Lavage(silica gel; elution with methanol)
9. 9
   Autreto give an oil
10. 10
    AutreCrystallization from ether
11. 11
    Autregave 0.54 g (4.5%) of white, crystalline solid, m.p. 75°-80° C.

Mode opératoire

A solution of 3.71 g (0.032 mole) of N,N-diethylethylenediamine and 5.83 (0.036 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 8.30 g (0.030 mole) of N-(2-propyl)-1-(phenylsulfonyl)-2-propanamine in 50 ml of tetrahydrofuran was added and the solution was refluxed overnight. The solvent was removed in vacuo, and the residue was partitioned between ether and water. The ether solution was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil. The oil was flash chromatographed (silica gel; elution with methanol) to give an oil. Crystallization from ether gave 0.54 g (4.5%) of white, crystalline solid, m.p. 75°-80° C.

Source