Dimethyl Sulfate → N,N,N-Trimethyl-1-adamantanaminium sulfate (2:1)

HRID 1621200Notes

Reaction equation

HRID 1621200 reaction equation
[C:1]12([N:11]([CH3:13])[CH3:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[S:14]([O:19]C)([O:17][CH3:18])(=[O:16])=[O:15]>O>[S:14]([O-:19])([O-:17])(=[O:16])=[O:15].[C:1]12([N+:11]([CH3:18])([CH3:13])[CH3:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2.[C:1]12([N+:11]([CH3:18])([CH3:13])[CH3:12])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 19478N,N-Dimethyl-1-adamantanamine

Product 1

HCID 67016445N,N,N-Trimethyl-1-adamantanaminium sulfate (2:1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A 2.5 m3 stirred vessel is charged with 2.5 t of water and 533 kg of 1-adamantyldimethylamine. Subsequently, 191 kg of dimethyl sulfate are metered in and the resulting reaction mixture is reacted at 30 to 50° C. for 2 hours. Subsequently the tank is heated to 140° C., an internal pressure of 4 bar being attained, and reaction continues at this temperature for 16 hours. The quaternization product is subjected to distillative removal of water, giving a 30% to 33% strength by weight solution of 1-adamantyltrimethylammonium sulfate. Conversion: 99%

Workup

  1. customthe resulting reaction mixture
  2. customis reacted at 30 to 50° C. for 2 hours
  3. customreaction
  4. customThe quaternization product is subjected to distillative removal of water

Sources & evidence

ORD record
ord-14b233a50ee448dc8708d4edcd495091
Source dataset
uspto-grants-2014_07
Patent number
US08772547B2

Reaction notes

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