Diethyl Ether → N,N-Bis(2-chloroethyl)benzylamine hydrochloride

HRID 265982

Reaction equation

HRID 265982 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]([CH2:16]CO)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(OCC)C.[CH:24]([Cl:27])(Cl)Cl>>[ClH:3].[Cl:3][CH2:6][CH2:7][N:8]([CH2:16][CH2:24][Cl:27])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 3283Diethyl EtherHCID 6212Chloroform2×HCID 75532,2'-((Phenylmethyl)imino)bisethanolHCID 24386Thionyl Chloride

Product 1

HCID 2777881N,N-Bis(2-chloroethyl)benzylamine hydrochloride

Procedure

Thionyl chloride (25.4 g, 130 mmol) and chloroform (20 mL) are combined. A solution of N,N-bis(2-hydroxyethyl)-N-benzylamine (25.4 g, 130 mmol) in chloroform (20 mL) is added dropwise over 1 hour. When the addition is complete the reaction mixture is refluxed for 1 hour. The reaction mixture is cooled to ambient temperature and diethyl ether was added to form a solid which is collected by filtration, rinsed with diethyl ether, and dried to give the title compound.

Workup

  1. additionWhen the addition
  2. temperatureis refluxed for 1 hour
  3. customto form a solid which
  4. filtrationis collected by filtration
  5. washrinsed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-296764c90a7140689aa64d02bd1858d6
Source dataset
uspto-grants-1997_07
Patent number
US05648366

Linked notes

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