(Diethylamino)trimethylsilane → 1,3-Dimethyl-2-dimethylaminoimidazolidinium methylsulfate

HRID 2116868Notes

Reaction equation

HRID 2116868 reaction equation
[CH2:1]([N:3]([Si](C)(C)C)[CH2:4][CH3:5])C.[CH3:10][O:11][S:12]([O-:15])(=[O:14])=[O:13].[CH3:16][NH+:17]1[CH2:21][CH2:20][N:19](C)[CH:18]1Cl>C(Cl)(Cl)Cl>[CH3:10][O:11][S:12]([O-:15])(=[O:14])=[O:13].[CH3:1][NH+:3]1[CH2:4][CH2:5][N:19]([CH3:20])[CH:18]1[N:17]([CH3:21])[CH3:16]

Participants

4

Reactant 2

HCID 70454(Diethylamino)trimethylsilaneHCID 866130351,3-Dimethyl-2-chloroimidazolidinium methylsulfate

Product 1

HCID 860638731,3-Dimethyl-2-dimethylaminoimidazolidinium methylsulfateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.33 g (11.34 mmol) of N,N-diethyltrimethylsilylamine are added over the course of 5 minutes at room temperature and with vigorous stirring to 2.50 g (10.22 mmol) of 1,3-dimethyl-2-chloroimidazolidinium methylsulfate in 10 ml of dry chloroform. The solvent is distilled off, and the residue is washed three times with 5 ml of diethyl ether and subsequently dried under a reduced pressure of 7.0 Pa and at 50° C. for 1 hour. The product is crystallised from a mixture of tetrahydrofuran:diethyl ether (1:1), giving 2.22 g of 1,3-dimethyl-2-dimethylaminoimidazolidinium methylsulfate, corresponding to a yield of 85.7%.

Workup

  1. distillationThe solvent is distilled off
  2. washthe residue is washed three times with 5 ml of diethyl ether
  3. customsubsequently dried under a reduced pressure of 7.0 Pa and at 50° C. for 1 hour
  4. customThe product is crystallised from a mixture of tetrahydrofuran:diethyl ether (1:1)

Sources & evidence

ORD record
ord-e276b8e455f548b9bc17de4f7ed3f01e
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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