4-Nitrobenzenesulfonyl chloride → HCID 13913712, compound

HRID 978806Notes

Reaction equation

HRID 978806 reaction equation
[CH:1]([NH:4][CH2:5][CH2:6][CH2:7][NH:8][CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(Cl)Cl>[CH3:10][CH:9]([N:8]([CH2:7][CH2:6][CH2:5][NH:4][CH:1]([CH3:3])[CH3:2])[S:21]([C:18]1[CH:17]=[CH:16][C:15]([N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=1)(=[O:22])=[O:23])[CH3:11]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 144018N,N'-Diisopropyl-1,3-propanediamine

Product 1

HCID 13913712HCID 13913712, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N,N'-diisopropyl propane-1,3-diamine (23.43 g) in methylene chloride was added p-nitrobenzenesulfonyl chloride (11.08 g, 0.05 mole) dropwise and the reaction stirred 2 hours. The reaction was filtered, stripped, the residue dissolved in diethyl ether, refiltered after washing with water and the contents of the filtrate chromatographed on dry column silica gel with ethyl acetate to provide 9.75 g of clear product as the free base. Preparation of hydrochloride salt gave 8.22 g, m.r. 183°-185° C.

Workup

  1. filtrationThe reaction was filtered
  2. dissolutionthe residue dissolved in diethyl ether
  3. washafter washing with water
  4. customthe contents of the filtrate chromatographed
  5. dry with materialon dry column silica gel with ethyl acetate

Sources & evidence

ORD record
ord-168e319ed8f446328d55bea432ac9b1f
Source dataset
uspto-grants-1987_05
Patent number
US04665227

Reaction notes

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