Putrescine → N,N'-bis(mesitylenesulfonyl)putrescine

HRID 10473

Reaction equation

HRID 10473 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][NH2:19]>C(Cl)Cl.[OH-].[Na+]>[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([NH:14][CH2:15][CH2:16][CH2:17][CH2:18][NH:19][S:9]([C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:13])(=[O:11])=[O:10])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 1045PutrescineHCID 130462-Mesitylenesulfonyl chloride

Product 1

HCID 10434030N,N'-bis(mesitylenesulfonyl)putrescineYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  1. customOrganic solvent was evaporated
  2. addition2.4 N HCl (250 ml) was added to the combined portions
  3. filtrationSolid was filtered
  4. washwashed with water (250 ml)
  5. customrecrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-1867737373ad4bb48701270e5edc5939
Source dataset
uspto-grants-2006_08
Patent number
US07094808B2

Linked notes

Loading…