Reacción #4326

Ecuación de reacción

methanol

1,1'-carbonyldiimidazole

N,N-diethylethylenediamine

N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine

→

brown oil

Rendimiento 66.6%

N'-[2-(Diethylamino)ethyl]-N-(1-methylethyl)-N-[5-(phenylsulfonyl)pentyl]urea hydrate

Rendimiento 66.6%

Disolventes

tetrahydrofuran

chloroform

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturathe resulting solution was heated over night at gentle reflux
3. 3
   ExtracciónThe chloroform layer was extracted with water
4. 4
   Secadodried (anhydrous sodium sulfate)
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed
7. 7
   Otroto give a brown oil
8. 8
   Lavadofor elution
9. 9
   Otrosolvent removed
10. 10
    Otrothe oil dried in vacuo at 60° C. overnight

Procedimiento

A solution of 1,1'-carbonyldiimidazole (4.54 g, 0.028 mole) and N,N-diethylethylenediamine (2.90 g, 0.025 mole) in tetrahydrofuran was stirred for 1 hr at room temperature. A solution of N-(1-methylethyl)-5-(phenylsulfonyl)-1-pentanamine (6.74 g, 0.025 mole) in tetrahydrofuran (dried over 4 A molecular sieves) was added and the resulting solution was heated over night at gentle reflux. The reaction mixture was stripped to dryness and the residue dissolved in chloroform. The chloroform layer was extracted with water, dried (anhydrous sodium sulfate), filtered and the solvent removed to give a brown oil. The brown oil was subjected to flash column chromatography on Silica Gel using methanol for elution. Fractions of similar purity were combined, solvent removed, and the oil dried in vacuo at 60° C. overnight. This produced 7.00 g (66.6% yield) of brown oil.

Fuente