Water → HCID 12814504, compound

HRID 1532585Notes

Reaction equation

HRID 1532585 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)
  7. customThe solvent was removed in vacuo
  8. customto give an oil which
  9. customdried in vacuo

Sources & evidence

ORD record
ord-3a71e465714d4e2aa2244f964e7de5c5
Source dataset
uspto-grants-2001_03
Patent number
US06204259B1

Reaction notes

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