2-Chloro-N,N-bis(2-chloroethyl)ethanamine → Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

HRID 2059139Notes

Reaction equation

HRID 2059139 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:8][CH2:9]Cl)[CH2:5][CH2:6]Cl.[CH3:11][O:12][CH2:13][CH2:14][OH:15]>>[CH2:3]([N:4]([CH2:8][CH2:9][O:15][CH2:14][CH2:13][O:12][CH3:11])[CH2:5][CH2:6][O:15][CH2:14][CH2:13][O:12][CH3:11])[CH2:2][O:15][CH2:14][CH2:13][O:12][CH3:11]

Participants

3

Reactant 2

HCID 55612-Chloro-N,N-bis(2-chloroethyl)ethanamineHCID 80192-Methoxyethanol

Product 1

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Procedure

To the aforesaid reaction mixture (i), 51.6 g tris(2-chloroethyl)amine chlorhydrate (0.215 moles) were added. The mixture was then heated with reflux of 2-methoxyethanol (125° C.) for 12 hours, followed by the distillation of the solvent under reduced pressure. The excess sodium 2-methoxyethanolate was then neutralized by addition of 11.6 cm3 aqueous HCl (10 N). The sodium chloride was filtered off and the solution distilled.

Workup

  1. additionwere added
  2. temperatureThe mixture was then heated
  3. distillationfollowed by the distillation of the solvent under reduced pressure
  4. additionThe excess sodium 2-methoxyethanolate was then neutralized by addition of 11.6 cm3 aqueous HCl (10 N)
  5. filtrationThe sodium chloride was filtered off
  6. distillationthe solution distilled

Sources & evidence

ORD record
ord-3afec1d7478842e7b19584f7dd5ff4f3
Source dataset
uspto-grants-1982_03
Patent number
US04322369

Reaction notes

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