Dichloromethane → N,N-bis(2-chloroethyl)methyl ammonium hydrochloride

HRID 1854520Notes

Reaction equation

HRID 1854520 reaction equation
[CH3:1][N:2]([CH2:6]CO)[CH2:3][CH2:4]O.S(Cl)([Cl:11])=O.[CH2:13]([Cl:15])Cl>>[ClH:11].[Cl:11][CH2:4][CH2:3][NH+:2]([CH3:6])[CH2:1][CH2:13][Cl:15]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 7767N-MethyldiethanolamineHCID 24386Thionyl Chloride

Product 1

HCID 71676372N,N-bis(2-chloroethyl)methyl ammonium hydrochlorideYield 85%

Procedure

A solution of N-methyldiethanolamine (3 g, 25 mmol) in CH2Cl2 (5 mL) was slowly added dropwise to thionyl chloride (10 mL) in ice-water bath, then stirred at r. t. for 2 days. After evaporated, the residue was dispersed with CH3CN/Et2O, then was filtered to give N,N-bis(2-chloroethyl)methyl ammonium hydrochloride (4.1 g, 85%).

Workup

  1. customAfter evaporated
  2. additionthe residue was dispersed with CH3CN/Et2O
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-441c7afbe3b5454e9271c4cc512024cc
Source dataset
uspto-grants-2015_02
Patent number
US08962670B2

Reaction notes

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