Diethylamine → N,N-diethyl-6-chlorohexanesulfonamide

HRID 565736Notes

Reaction equation

HRID 565736 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8](Cl)(=[O:10])=[O:9].[CH2:12]([NH:14][CH2:15][CH3:16])[CH3:13]>C(OCC)C>[CH2:12]([N:14]([CH2:15][CH3:16])[S:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])(=[O:10])=[O:9])[CH3:13]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 110639276-Chlorohexanesulfonyl chloride

Product 1

HCID 22111559N,N-diethyl-6-chlorohexanesulfonamideYield 92.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6-Chlorohexanesulfonyl chloride (6.57g, 30 mmol) was added dropwise to a solution of diethyl ether (60 ml) and diethylamine (4.83g, 66 mmol) with stirring under ice-cooling. Thereafter, the mixture was stirred at the same temperature for 20 minutes. The reaction mixture was washed twice with water (10 ml) and then with brine (10 ml), and thereafter dried over anhydrous magnesium sulfate. Subsequently, the solvent was removed by evaporation In vacuo. The crude product was purified by column chromatography on silica gel with ethyl acetate-n-hexane (1:4), to give N,N-diethyl-6-chlorohexanesulfonamide (7.12 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringThereafter, the mixture was stirred at the same temperature for 20 minutes
  3. washThe reaction mixture was washed twice with water (10 ml)
  4. dry with materialwith brine (10 ml), and thereafter dried over anhydrous magnesium sulfate
  5. customSubsequently, the solvent was removed by evaporation In vacuo
  6. customThe crude product was purified by column chromatography on silica gel with ethyl acetate-n-hexane (1:4)

Sources & evidence

ORD record
ord-cab9efaabb284ef48d63ed856945cdea
Source dataset
uspto-grants-2001_01
Patent number
US06172228B2

Reaction notes

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