Reacción #10569

Ecuación de reacción

2-Mesitylenesulfonyl chloride

1,4-diaminobutane

→

( 1 )

Rendimiento 90.0%

N,N′-bis-(mesitylenesulfonyl)putrescine

Rendimiento 90.0%

Disolventes

CH2Cl2

NaOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroOrganic solvent was evaporated
2. 2
   workup.ADDITION2.4 N HCl (250 ml) was added to the combined portions
3. 3
   FiltraciónSolid was filtered
4. 4
   Lavadowashed with water (250 ml)
5. 5
   Otrorecrystallized from aqueous ethanol

Procedimiento

2-Mesitylenesulfonyl chloride (54.40 g, 0.249 mol) in CH2Cl2 (300 ml) was added to 1,4-diaminobutane (11.34 g, 0.129 mol) in 1 N NaOH (300 ml) at 0° C., and the biphasic mixture was stirred for 24 hours at room temperature. Organic solvent was evaporated and 2.4 N HCl (250 ml) was added to the combined portions. Solid was filtered, washed with water (250 ml) and recrystallized from aqueous ethanol to give 50.46 g (90%) of (1) as needles: mp 156.5-157.5° C.; NMR (CDCl3/TMS) δ 1.36-1.60 (m, 4H), 2.27 (s, 6H), 2.57 (s, 12H), 2.69-2.96 (m, 4H), 4.65 (t, 2H, J=6), 6.89 (s, 4H). Anal. calcd. for C22H32N2O4S2: C—58.38, H—7.13, N—6.19. Found: C—58.31, H—7.19, N—6.14.

Fuente