Dimethylamine → ((Dimethylamino)methylene)dimethylammonium methyl sulphate

HRID 588282Notes

Reaction equation

HRID 588282 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.[CH3:6][O:7][S:8]([O:11]C)(=[O:10])=[O:9].[CH3:13][NH:14][CH3:15]>C1COCC1.C1(C)C=CC=CC=1>[CH3:6][O:7][S:8]([O-:11])(=[O:10])=[O:9].[CH3:1][N:2]([CH3:5])[CH:3]=[N+:14]([CH3:15])[CH3:13]

Participants

6

Reactant 3

HCID 674DimethylamineHCID 6228DimethylformamideHCID 6497Dimethyl Sulfate

Product 1

HCID 3014065((Dimethylamino)methylene)dimethylammonium methyl sulphate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N.N-dimethylformamide (7.31 g) and dimethylsulfate (12.60 g) are heated to 60° C. for 4 h. Then dimethylamine in THF (100 ml, 2 M solution) and toluene (15 ml) are added and the resulting mixture is stirred at reflux for 1 h. The reaction mixture is cooled to room temperature and the phases are separated. The lower layer is washed three times with anhydrous tert-butyl methyl ether to give N,N,N′,N′-tetramethylformamidinium methylsulfate (18, R6=Me, R7=Me). 1H NMR (C6D6), 7.95 (1H), 3.70 (3H), 3.32 (6H), 3.29 (6H).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureThe reaction mixture is cooled to room temperature
  3. customthe phases are separated
  4. washThe lower layer is washed three times with anhydrous tert-butyl methyl ether

Sources & evidence

ORD record
ord-b86ca782ca424097abae70d6b09ff5d8
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Reaction notes

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