4-Toluenesulfonyl chloride → HCID 4135031, compound

HRID 1707831Notes

Reaction equation

HRID 1707831 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1>N1C=CC=CC=1>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:16]([C:13]2[CH:14]=[CH:15][C:10]([CH3:20])=[CH:11][CH:12]=2)(=[O:18])=[O:17])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 695331,7-Heptanediamine

Product 1

HCID 4135031HCID 4135031, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 1,9-diazanonane (13g, 0.1 mol) in pyridine (50 mL) and cool to ° C. Add, in portions, p-toluenesulfonyl chloride (41.9 g, 0.22 mol) and stir overnight. Extract into chloroform, wash with water, 5% hydrochloric acid, water and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography to give 1,9-bis[(4-methylphenyl)sulfonyl]-1,9-diazanonane.

Workup

  1. temperaturecool
  2. extractionExtract into chloroform
  3. washwash with water, 5% hydrochloric acid, water
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo
  6. custompurify by silica gel chromatography

Sources & evidence

ORD record
ord-181dda60085748769a5b55f72abe050d
Source dataset
uspto-grants-1994_10
Patent number
US05354782

Reaction notes

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