Toluene → N,N,N',N'-tetramethylformamidinium para-toluenesulfonate

HRID 588284Notes

Reaction equation

HRID 588284 reaction equation
[CH2:1]([N:3]([CH2:6]C)[CH:4]=O)C.C[O:9][S:10]([O:13]C)(=O)=[O:11].[CH2:15]([NH:17][CH2:18]C)C.[C:20]1([CH3:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[C:20]1([CH3:26])[CH:25]=[CH:24][C:23]([S:10]([O-:13])(=[O:11])=[O:9])=[CH:22][CH:21]=1.[CH3:1][N:3]([CH3:6])[CH:4]=[N+:17]([CH3:18])[CH3:15]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 8021DiethylamineHCID 12051Diethylformamide

Product 1

HCID 86651391N,N,N',N'-tetramethylformamidinium para-toluenesulfonate

Conditions

Temperature
50 °C

Procedure

A mixture of N.N-diethylformamide (30 g) and dimethylsulfate (37.5 g) are heated to 50° C. for 4 h. Then a mixture of diethylamine (32.6 g) and toluene (20 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 ten times with diethyl ether to give N,N,N′,N′-tetraethylformamidinium methylsulfate (18, R6=Et, R7=Et). 1H NMR (DMSO-d6), 7.26 (1H), 3.51 (8H), 3.42 (3H), 1.24 (12H) ppm.

Workup

  1. additionare added
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture is cooled to room temperature
  4. customthe phases are separated
  5. washThe lower layer is washed ten times with diethyl ether

Sources & evidence

ORD record
ord-c02b89abbf0e4d36ac337a5312dcd51c
Source dataset
uspto-grants-2016_01
Patent number
US09227934B2

Reaction notes

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