Sulfuryl chloride → 2-[(Chlorosulfonyl)(methyl)amino]-N,N-dimethylethanaminium chloride

HRID 251725Notes

Reaction equation

HRID 251725 reaction equation
[S:1]([Cl:5])([Cl:4])(=[O:3])=[O:2].[CH3:6][NH:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11]>C(Cl)(Cl)Cl>[Cl-:4].[Cl:5][S:1]([N:7]([CH3:6])[CH2:8][CH2:9][NH+:10]([CH3:12])[CH3:11])(=[O:3])=[O:2]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-

Product 1

HCID 866279522-[(Chlorosulfonyl)(methyl)amino]-N,N-dimethylethanaminium chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of sulfuryl chloride (1.0 eq.) in CHCl3 at 0° C. was added dropwise trimethylethylenediamine (1.0 eq.) over 15 mins. After the addition, the cooling bath was removed and the mixture was stirred overnight at RT. The solvent was removed under reduced pressure and the residue was left under high vacuum for 4 h. The crude product was obtained as a pale yellow solid and was used without further purification. 1H NMR (300 MHz, DMSO-d6) δ: 3.46-3.29 (4H, m), 2.83 (6H, s), 2.60 (3H, s).

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. customThe solvent was removed under reduced pressure
  4. waitthe residue was left under high vacuum for 4 h

Sources & evidence

ORD record
ord-8e19611201884840a2fe3fe5ea13f657
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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