Pentamethylsilylamine → Bis(dimethylamino)-N,N-dimethylmethaniminium methyl sulfate

HRID 2116864Notes

Reaction equation

HRID 2116864 reaction equation
[CH3:1][N:2]([Si](C)(C)C)[CH3:3].[CH3:8][O:9][S:10]([O-:13])(=[O:12])=[O:11].[CH3:14][N:15]([C+:17]([N:19]([CH3:21])[CH3:20])Cl)[CH3:16]>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:3])[C:17](=[N+:15]([CH3:16])[CH3:14])[N:19]([CH3:21])[CH3:20].[CH3:8][O:9][S:10]([O-:13])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 74965PentamethylsilylamineHCID 178483689HCID 178483689, compound

Product 1

HCID 13127877Bis(dimethylamino)-N,N-dimethylmethaniminium methyl sulfateYield 95.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10 ml of dry chloroform and 1.29 g (11.00 mmol) of N,N-dimethyltrimethylsilylamine are added to 2.45 g (9.93 mmol) of bis(dimethylamino)chlorocarbenium methylsulfate. The reaction mixture is stirred for 1 hour at room temperature, and all volatile compounds are subsequently removed under reduced pressure. The residue is dried for a further 1 hour under reduced pressure at 7.0 Pa and an oil-bath temperature of 50° C., giving 2.42 g of hexamethylguanidinium methylsulfate, corresponding to a yield of 95.5%.

Workup

  1. customall volatile compounds are subsequently removed under reduced pressure
  2. customThe residue is dried for a further 1 hour under reduced pressure at 7.0 Pa and an oil-bath temperature of 50° C.

Sources & evidence

ORD record
ord-53f587e8cfe14d7ba855527992d01d50
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

Loading…