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

HRID 472115Notes

Reaction equation

HRID 472115 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

8.6 ml (62 mmol) of triethylamine are added to a solution of 5 g (28 mmol) of bis(2-chloroethyl)amine hydrochloride in 60 ml of dichloromethane. The triethylammonium chloride salts precipitate and are filtered off. 2.4 ml (31 mmol) of methylsulfonyl chloride are then added to the filtrate obtained, and the reaction medium is stirred at ambient temperature for 3 h. After the addition of water, the product is extracted with dichloromethane. The organic phase is washed with water, dried over magnesium sulfate, filtered and concentrated. 5.8 g (94%) of N,N-bis(2-chloroethyl)methanesulfonamide are obtained in the form of a beige solid.

Workup

  1. customThe triethylammonium chloride salts precipitate
  2. filtrationare filtered off
  3. customobtained
  4. extractionthe product is extracted with dichloromethane
  5. washThe organic phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c23fea10b8c8460482d90af57405a441
Source dataset
uspto-grants-2014_01
Patent number
US08633196B2

Reaction notes

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