4-Toluenesulfonyl chloride → HCID 19956415, compound

HRID 1779541Notes

Reaction equation

HRID 1779541 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][CH2:15][NH:16][CH2:17]/[CH:18]=[CH:19]/[CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH2:25].[OH-:26].[Na+]>C(Cl)Cl>[S:7]([NH:25][CH2:24][CH2:23][CH2:22][N:21]([S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:20]/[CH:19]=[CH:18]/[CH2:17][N:16]([S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8])[CH2:15][CH2:14][CH2:13][NH:12][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:8])=[O:26])([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 5869833N,N'-BIS(3-AMINOPROPYL)-2-BUTENE-1,4-DIAMINE

Product 1

HCID 19956415HCID 19956415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 38.13 g (0.2 mol) of p-toluenesulfonic acid chloride in 300 ml of methylene chloride is added dropwise at room temperature, with stirring and under a nitrogen atmosphere, to a solution of 10.02 g (0.05 mol) of (E)-1,5,10,14-tetraazatetradec-7-ene in 100 ml (0.2 mol) of 2N sodium hydroxide solution. The reaction mixture is stirred for a further 2 h at room temperature, and then the organic phase is separated off and the aqueous phase is extracted with methylene chloride. The organic phases are combined, washed with water, dried over sodium sulfate and concentrated by evaporation. The residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm, using ethyl acetate-hexane (1:1). Concentration of the product-containing fractions by evaporation yields the title compound in the form of an amorphous residue, Rf value=0.51 (silica gel/methylene chloride:methanol (50:1)).

Workup

  1. customthe organic phase is separated off
  2. extractionthe aqueous phase is extracted with methylene chloride
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by means of flash chromatography over silica gel having a particle size of 0.04-0.063 mm
  7. customConcentration of the product-containing fractions by evaporation

Sources & evidence

ORD record
ord-23b603d8a38e40ada212877af07bfa51
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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