Water → HCID 12814504, compound

HRID 2287802Notes

Reaction equation

HRID 2287802 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.[NH2:12][CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][NH:19][CH2:20][CH2:21][NH2:22].[OH2:23]>N1C=CC=CC=1.C(Cl)Cl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([NH:22][CH2:21][CH2:20][N:19]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:18][CH2:17][CH2:16][N:15]([S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:14][CH2:13][NH:12][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:8])=[O:23])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 78479N,N'-Bis(2-aminoethyl)-1,3-propanediamine

Product 1

HCID 12814504HCID 12814504, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of p-toluenesulfonyl chloride (262 g, 1.37 mole) in anhydrous pyridine (600 ml) at 5° C. was added a solution of 1,4,8,11-tetraazaundecane (49.1 g, 0.306 mole) in anhydrous pyridine (200 ml) under a dry argon atmosphere, maintaining the temperature <20° C. The addition required 1 h. The mixture was stirred overnight at room temperature. H2O (1.5 l) was slowly added to the cooled (ice bath) mixture. The resulting oil was dissolved in CH2Cl2, separated from the aqueous layer. The CH2Cl2 layer was washed with 5% HCl and H2O and dried (MgSO4) The solvent was removed in vacuo to give an oil which solidified on standing. The resulting solid was ground to a powder and dried in vacuo to give 186 g (78% yield) of the crude product: 1H NMR (CDCl3) δ 1.98 (quint, J=7.3 Hz, 2 H), 2.40 (s, 6 H), 2.42 (s, 6 H), 3.11 (t, J=7.3 Hz, 4 H), 3.17 (s, 8 H), 5.76 (t, J=6.0 Hz, 2 H), 7.29 (m, 8 H), 7.64 (d, J=8.3 Hz, 4 H), 7.75 (d, J=8.3 Hz, 4 H).

Workup

  1. temperaturemaintaining the temperature <20° C
  2. additionThe addition required 1 h
  3. temperaturecooled (ice bath) mixture
  4. customseparated from the aqueous layer
  5. washThe CH2Cl2 layer was washed with 5% HCl and H2O
  6. dry with materialdried (MgSO4) The solvent
  7. customwas removed in vacuo
  8. customto give an oil which
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d20bead7473d40e28a1056d11f81d7d9
Source dataset
uspto-grants-2000_07
Patent number
US06084093

Reaction notes

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