Diethylamine → HCID 178464166, compound

HRID 2116854Notes

Reaction equation

HRID 2116854 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[S:6]([O-:10])([OH:9])(=[O:8])=[O:7].[CH3:11][N:12]([C+:14]([N:16]([CH3:18])[CH3:17])Cl)[CH3:13]>O>[S:6]([O-:10])([OH:9])(=[O:8])=[O:7].[CH3:11][N:12]([CH3:13])[C:14]([N:16]([CH3:18])[CH3:17])=[N+:3]([CH2:4][CH3:5])[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 178483698HCID 178483698, compound

Product 1

HCID 178464166HCID 178464166, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.20 g (57.4 mmol) of diethylamine are added with stirring and ice-cooling to 6.00 g (25.8 mmol) of bis(dimethylamino)chlorocarbenium hydrogensulfate. The reaction mixture is subsequently stirred for 1 hour at room temperature, and 50 ml of water are subsequently added. The organic phase is separated off, and the aqueous phase is extracted with 50 ml of dichloromethane. The combined organic phases are washed with 20 ml of water, and the solvent is distilled off under reduced pressure. The residue is subsequently dried at 50° C. under reduced pressure (7.0 Pa), giving 5.7 g of viscous N,N,N′,N′-tetramethyl-N″,N″-diethylguanidinium hydrogensulfate, corresponding to a yield of 82.0%.

Workup

  1. stirringThe reaction mixture is subsequently stirred for 1 hour at room temperature
  2. customThe organic phase is separated off
  3. extractionthe aqueous phase is extracted with 50 ml of dichloromethane
  4. washThe combined organic phases are washed with 20 ml of water
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue is subsequently dried at 50° C. under reduced pressure (7.0 Pa)

Sources & evidence

ORD record
ord-06865c6a7fdf4adbafc3d1d72a22bec5
Source dataset
uspto-grants-2008_10
Patent number
US07439395B2

Reaction notes

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