1,4-Dibromobutane → HCID 67275763, compound

HRID 1698505Notes

Reaction equation

HRID 1698505 reaction equation
[CH2:1]([N:4]([CH2:20][CH:21]=[CH2:22])[CH:5]([C:8]1[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])=[CH:10][CH:9]=1)[CH2:6][NH2:7])[CH:2]=[CH2:3].Br[CH2:24][CH2:25][CH2:26][CH2:27]Br.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CO>[NH3:4].[CH2:20]([N:4]([CH2:1][CH:2]=[CH2:3])[CH:5]([C:8]1[CH:9]=[CH:10][C:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:15])=[O:16])=[CH:12][CH:13]=1)[CH2:6][N:7]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH:21]=[CH2:22]

Participants

7

Reactant 3

HCID 80561,4-DibromobutaneHCID 516892Sodium BicarbonateHCID 86635958N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

Product 2

HCID 222AmmoniaHCID 67275763HCID 67275763, compoundYield 102.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine (445 mg, 1.38 mmol), 1,4-dibromobutane (0.18 mL, 1.51 mmol) and sodium hydrogencarbonate (0.26 g, 3.09 mmol) were heated in toluene at reflux for 17 h. The reaction mixture was allowed to cool to ambient temperature, filtered through Celite and the filter cake washed with ethyl acetate. The filtrate was washed with water and then brine before being dried (MgSO4) and concentrated. The crude product was purified using an SCX cartridge eluting with dichloromethane, then methanol and finally 2M ammonia in methanol to give the title compound as a pale yellow oil (266 mg, 51% yield). 1H NMR (400 MHz, CDCl3) δ 1.00 (3H, t, J=7.5 Hz), 1.69-1.80 (6H, m), 2.45-2.54 (4H, m), 2.83-3.00 (4H, m), 3.05-3.09 (2H, m), 3.21 (2H, dd, J=14.4, 6.0 Hz), 4.07 (1H, dd, J=8.3, 5.2 Hz), 5.11-5.19 (4H, m), 5.76-5.84 (2H, m), 7.58 (2H, d, J=8.3 Hz), 7.83 (2H, d, J=8.4 Hz); m/z (ES+) 377 (M+H), 280 (M−N[allyl]2).

Workup

  1. temperatureat reflux for 17 h
  2. filtrationfiltered through Celite
  3. washthe filter cake washed with ethyl acetate
  4. washThe filtrate was washed with water
  5. dry with materialbrine before being dried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was purified
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-6180fd3c60394b43aad6159af7219bda
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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