Sulfuric Acid → N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

HRID 1698504Notes

Reaction equation

HRID 1698504 reaction equation
S(=O)(=O)(O)O.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:12]([N:15]([CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH2:31][CH2:32][CH3:33])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[C:20]#[N:21])[CH2:16][CH:17]=[CH2:18])[CH:13]=[CH2:14].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:16]([N:15]([CH2:12][CH:13]=[CH2:14])[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([CH2:31][CH2:32][CH3:33])(=[O:29])=[O:30])=[CH:26][CH:27]=1)[CH2:20][NH2:21])[CH:17]=[CH2:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 67276212HCID 67276212, compound

Product 1

HCID 86635958N1,N1-Diallyl-1-[4-(propylsulphonyl)phenyl]ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Anhydrous THF (5 mL) was cooled to 0° C. and treated with 98% sulphuric acid (0.28 mL, 5.25 mmol). After stirring for 15 mins, lithium aluminium hydride (10.5 mL of 1.0M solution in THF, 10.5 mmol) was added drop wise over 10 mins. The mixture was stirred at 0° C. for 60 minutes before addition of a solution of (diallylamino)[4-(propylsulphonyl)phenyl]acetonitrile (1.22 g, 3.83 mmol) in THF (3+2 mL washing). The mixture was stirred at 0° C. for 30 mins then at 40° C. for 1 h. The reaction was allowed to cool and carefully treated with powdered sodium sulphate decahydrate (3 g). The mixture was stirred at ambient temperature for 15 h, then filtered and the filtrate concentrated to give a pale yellow oil. Used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.01 (3H, t, J=7.4 Hz), 1.75-1.81 (2H, m), 2.82 (2H, dd, J=14.6, 7.6 Hz), 2.95 (1H, dd, J=13.0, 6.0 Hz), 3.06-3.10 (2H, m), 3.18 (1H, dd, J=13.1, 7.5 Hz), 3.28-3.33 (2H, m), 3.86 (1H, br t, J=67 Hz), 5.15-5.20 (4H, m), 5.77-5.85 (2H, m), 7.44 (2H, d, J=8.3 Hz), 7.88 (2H, d, J=8.3 Hz); m/z (ES+) 323 (M+H), 306 (M−NH2).

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 mins
  2. waitat 40° C. for 1 h
  3. temperatureto cool
  4. stirringThe mixture was stirred at ambient temperature for 15 h
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customto give a pale yellow oil
  8. customUsed without further purification

Sources & evidence

ORD record
ord-05a939d0544f4710b19cc135a8f48733
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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