4-Toluenesulfonyl chloride → N,N'-Di(p-toluenesulfonyl)-1,2-diamino-3-phenylpropane

HRID 976176Notes

Reaction equation

HRID 976176 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C(N([CH2:17][CH3:18])CC)C.[NH2:19][CH2:20][CH:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:19][CH2:20][CH:21]([NH:29][S:7]([C:4]2[CH:5]=[CH:6][C:17]([CH3:18])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 4134343-Phenylpropane-1,2-diamine

Product 1

HCID 18705612N,N'-Di(p-toluenesulfonyl)-1,2-diamino-3-phenylpropaneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of p-toluenesulfonyl chloride (92.0 g, 0.482 mole) and triethylamine (48.8 g, 0.482 mole) in CH2Cl2 (350 ml) at 0° C. under a dry argon atmosphere was added a solution of 1,2-diamino-3-phenylpropane prepared as in Example 6A (34.5 g, 0.230 mole) in CH2Cl2 (100 ml), maintaining the temperature <10° C. The addition required 1 h. The mixture was allowed to warm to room temperature and was stirred an additional 15 h. The mixture was then poured onto ice (500 g) and the CH2Cl2 layer was separated. The CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution and was dried (MgSO4). The solvent was removed in vacuo and the resulting yellow oil washed with hexane. The crude product was purified by recrystallization from CH2Cl2 -hexane to give 71.4 g (68% yield) of the product as a crystalline solid: mp 128°-31° C.; 1H NMR (CDCl3) δ2.42 (s, 3 H), 2.43 (s, 3 H), 2.69 (ABq of dd, δν=44.0 Hz, J=14.0, 6.6 HZ, 2 H), 3.02 (m, 2 H), 3.36 (hex, J=6.6 Hz, 2 H), 4.85 (d, J=6.6 Hz, 1 H), 5.16 (t, J=6.5 Hz, 1 H), 6.87 (m, 2 H), 7.15 (m, 5 H), 7.29 (m, 2 H), 7.50 (m, 2 H), 7.70 (m, 2 H).

Workup

  1. temperaturemaintaining the temperature <10° C
  2. additionThe addition required 1 h
  3. additionThe mixture was then poured onto ice (500 g)
  4. customthe CH2Cl2 layer was separated
  5. washThe CH2Cl2 layer was washed with 1N HCl, H2O and saturated NaCl solution
  6. dry with materialwas dried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. washthe resulting yellow oil washed with hexane
  9. customThe crude product was purified by recrystallization from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-43415bee02a5447b9b9ed71d5e3ee3d4
Source dataset
uspto-grants-1997_03
Patent number
US05610293

Reaction notes

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