Ethanol, 2,2'-(1,2-ethanediyldiimino)bis- → 1,2-Ethanediamine, N,N'-bis(2-chloroethyl)-, dihydrochloride

HRID 742387Notes

Reaction equation

HRID 742387 reaction equation
[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][Cl:10].OCCNCCNCCO>O=S(Cl)Cl>[ClH:1].[ClH:1].[Cl:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][Cl:10]

Participants

4

Reactant 2

HCID 78179Ethanol, 2,2'-(1,2-ethanediyldiimino)bis-HCID 409899N,N'-Bis(2-chloroethyl)ethylenediamine

Product 1

HCID 30474461,2-Ethanediamine, N,N'-bis(2-chloroethyl)-, dihydrochloride

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

N,N'-Bis(2-chloroethyl)ethylenediamine (BCE) A solution of N,N'-bis(2-hydroxyethyl)ethylenediamine (5.4 g, 0.036 mol) in SOCl2 (60 mL) was heated at 90° C. for 2 h, then stirred at room temperature for 24 h. Excess SOCl2 was then removed under reduced pressure, and the residue was triturated with isopropanol. Crystallisation from boiling isopropanol (800 mL) containing just enough water to dissolve the solids gave N,N'-bis(2-chloroethyl)ethylenediamine dihydrochloride (BCE.2HCl).

Workup

  1. customExcess SOCl2 was then removed under reduced pressure
  2. customthe residue was triturated with isopropanol
  3. customCrystallisation
  4. additioncontaining just enough water
  5. dissolutionto dissolve the solids

Sources & evidence

ORD record
ord-69d12510b9c14d179279c2e24e7d2eb4
Source dataset
uspto-grants-1996_09
Patent number
US05554648

Reaction notes

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