Water → Bis(2-chloroethyl)ethylamine

HRID 517519

Reaction equation

HRID 517519 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([N:7]([CH2:11]CO)[CH2:8][CH2:9]O)[CH3:6].O.C(=O)([O-])O.[Na+].Cl[CH2:21][Cl:22]>>[Cl:3][CH2:9][CH2:8][N:7]([CH2:11][CH2:21][Cl:22])[CH2:5][CH3:6]

Participants

6

Reactant 5

HCID 962WaterHCID 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 to a solution of 20 g (150 mmol) of 2-[ethyl-(2-hydroxy-ethyl)amino]ethanol in 200 ml of dichloromethane cooled to 0° C. The reaction medium is stirred at ambient temperature for 20 h. After addition of 50 ml of water then gradual addition of a saturated aqueous solution of sodium hydrogen carbonate up to a pH of 7, the reaction medium is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated under vacuum. 19.5 g (76%) of bis(2-chloroethyl)ethylamine are obtained in the form of a brown oil.

Workup

  1. extractionthe reaction medium is extracted with dichloromethane
  2. washThe organic phase is washed with water
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3d33994b4fc84cf9933995d033aa52da
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Linked notes

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