Propylenediamine → HCID 2932603, compound

HRID 363376Notes

Reaction equation

HRID 363376 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]([NH2:23])[CH3:22]>C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:19][CH2:20][CH:21]([NH:23][S:7]([C:4]2[CH:5]=[CH:6][C:17]([CH3:18])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH3:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6567PropylenediamineHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 2932603HCID 2932603, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of p-toluenesulfonyl chloride (270 g, 1.42 mole) and triethylamine (143 g, 1.42 mole) in CH2Cl2 (1.0 l) at 0° C. under a dry argon atmosphere was added a solution of 1,2-diaminopropane (50.0 g, 0.675 mole) in CH2Cl2 (250 ml) dropwise, maintaining the temperature <10° C. The addition required 1 h. The mixture was allowed to warm to room temperature and was stirred an additional 19 h. The mixture was poured onto ice (1000 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 was washed with hexane. The crude product was purified by recrystallization from CH2Cl2 -hexane to give 241 g (93% yield) of the product as colorless needles: mp 105°-7° C.; 1H NMR(CDC13) δ 0.97 (d, J=6.7 Hz, 3 H), 2.40 (s, 3 H), 2.41 (s, 3 H), 2.91 (m, 2 H), 3.32 (m, 1 H), 5.25 (d, J=7.6 Hz, 1 H), 5.38 (t, J=6.3 Hz, 1 H), 7.28 (m, 4 H) 7.73, (m, 4 H).

Workup

  1. temperaturemaintaining the temperature <10° C
  2. additionThe addition required 1 h
  3. additionThe mixture was poured onto ice (1000 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 was washed with hexane
  9. customThe crude product was purified by recrystallization from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-bdd0bb28950b48b68ad8e9c6878f49dd
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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