Water → n,n-Bis(2-chloroethyl)methanesulfonamide

HRID 517499Notes

Reaction equation

HRID 517499 reaction equation
C(N(CC)CC)C.Cl.[Cl:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][Cl:15].[CH3:16][S:17](Cl)(=[O:19])=[O:18].O>ClCCl>[Cl:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][Cl:15])[S:17]([CH3:16])(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 522769Bis(2-chloroethyl)amine hydrochloride

Product 1

HCID 245092n,n-Bis(2-chloroethyl)methanesulfonamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

17 ml (123.2 mmol) of triethylamine are added to a solution of 10 g (56 mmol) of bis(2-chloroethyl)amine hydrochloride in 100 ml of dichloromethane. After filtration of the salts, 4.6 ml (58.8 mmol) of methanesulphonyl chloride are added to the filtrate obtained and the reaction medium is stirred at ambient temperature for 3 h. After addition of water, the product is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulphate, filtered and concentrated. 11.6 g (94%) of N,N-bis(2-chloroethyl)methanesulphonamide are obtained in the form of a beige solid.

Workup

  1. additionare added to the filtrate
  2. customobtained
  3. extractionthe product is extracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-305dbb57332b437aa59319c1fc614c20
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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