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

HRID 1619106Notes

Reaction equation

HRID 1619106 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]>ClCCl>[Cl:9][CH2:10][CH2:11][N:12]([CH2:13][CH2:14][Cl:15])[S:17]([CH3:16])(=[O:19])=[O:18]

Participants

5

Reactant 3

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

Product 1

HCID 245092n,n-Bis(2-chloroethyl)methanesulfonamideYield 743.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3.1 mL, 22.2 mmol) was added dropwise to a suspension of N,N-bis(2-chloroethyl)amine hydrochloride (2.0 g, 11.2 mmol) in dichloromethane and the mixture was stirred at room temperature for 20 minutes. The mixture was then cooled in an ice bath and methanesulfonyl chloride (1.41 g, 1.1 mmol) was added dropwise. The cooling bath was removed and the mixture was stirred for 4 hours at room temperature. Water was added to the reaction mixture and the organic layer was washed with 2M aqueous hydrochloric acid, water, dried (MgSO4) and evaporated to give the title compound (1.80 g, 73%) as a white solid.

Workup

  1. temperatureThe mixture was then cooled in an ice bath
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred for 4 hours at room temperature
  4. additionWater was added to the reaction mixture
  5. washthe organic layer was washed with 2M aqueous hydrochloric acid, water
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-1a75af30620b44fabca6bcb7273f41d7
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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