Dimethyl Sulfate → N,N,N-trimethyl-2-[methyl(4-nitrophenyl)-amino]ethanaminium methylsulfate

HRID 2109964Notes

Reaction equation

HRID 2109964 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[S:17]([O:22]C)([O:20][CH3:21])(=[O:19])=[O:18]>C(#N)C>[CH3:21][O:20][S:17]([O-:22])(=[O:19])=[O:18].[CH3:1][N+:2]([CH3:21])([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 21873305N,N,N'-trimethyl-N'-(4-nitrophenyl)-1,2-ethanediamine

Product 1

HCID 18522685N,N,N-trimethyl-2-[methyl(4-nitrophenyl)-amino]ethanaminium methylsulfate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8.0 g (36 mmol) of the compound from Step 9.1 was dissolved in 50 mL of acetonitrile and to the solution was added dropwise 4.55 g (36 mmol) of dimethyl sulfate over a period of 5 minutes with agitation which caused the reaction mixture to warm up slightly while the product gradually separated in crystalline form. The mixture was allowed to agitate for an additional 3 hours at room temperature after which it was suction-filtered. The filter cake was washed with a small amount of acetonitrile and then dried at 40° C. under vacuum. This gave 11.0 g (88% of the theoretical) of yellow crystals.

Workup

  1. temperatureto warm up slightly while the product
  2. customgradually separated in crystalline form
  3. filtrationwas suction-filtered
  4. washThe filter cake was washed with a small amount of acetonitrile
  5. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-b4f72a53682749d4a49896e4ea9899e4
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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