Dichloromethane → Bis(2-chloroethyl)ethylamine

HRID 2202192Notes

Reaction equation

HRID 2202192 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]([CH2:11]CO)[CH2:8][CH2:9]O)[CH3:6].C(=O)([O-])O.[Na+].Cl[CH2:20][Cl:21]>>[Cl:3][CH2:9][CH2:8][N:7]([CH2:11][CH2:20][Cl:21])[CH2:5][CH3:6]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8769EthyldiethanolamineHCID 24386Thionyl ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 10848Bis(2-chloroethyl)ethylamineYield 76%

Conditions

Temperature
0 °C

Procedure

24 ml (330 mmol) of thionyl chloride are added dropwise to a solution of 20 g (150 mmol) of 2-[ethyl(2-hydroxyethyl)amino]ethanol in 200 ml of dichloromethane cooled beforehand to 0° C., and then the reaction medium is stirred at ambient temperature for 20 h. After the addition of a saturated aqueous solution of sodium hydrogen carbonate, the product is extracted with dichloromethane. The organic phase obtained is then washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. 19.5 g (76%) of bis(2-chloroethyl)ethylamine are obtained in the form of an oil.

Workup

  1. extractionthe product is extracted with dichloromethane
  2. customThe organic phase obtained
  3. washis then washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c07b0c5aaaf34f73ad76b40fd4b5ca03
Source dataset
uspto-grants-2016_06
Patent number
US09365529B2

Reaction notes

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