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

HRID 2174839Notes

Reaction equation

HRID 2174839 reaction equation
[CH:1]([N:3]1[CH2:7]CC[CH2:4]1)=O.C[O:9][S:10]([O:13]C)(=O)=[O:11].[NH:15]1[CH2:19]CC[CH2:16]1.[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]([CH3:7])[CH:4]=[N+:15]([CH3:19])[CH3:16]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 31268PyrrolidineHCID 773721-Pyrrolidinecarboxaldehyde

Product 1

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

Conditions

Temperature
80 °C

Procedure

A mixture of N-formylpyrrolidine (100 g) and dimethylsulfate (126 g) are heated to 80° C. for 4 h. Then a mixture of pyrrolidine (71 g) and toluene (100 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 concentrated in vacuo and triturated with diethyl ester. The precipitate is collected by filtration and recrystallised using ethyl acetate to give 1-pyrrolidin-1-ylmethylene-pyrrolidinium methylsulfate (18, R6/R7=Pyrrolidinyl). 1H NMR (DMSO-d6), 8.28 (1H), 3.90-3.85 (4H), 3.68-3.62 (4H), 3.38 (3H), 1.99-1.90 (4H), 1.86-1.77 (4H).

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. concentrationThe lower layer is concentrated in vacuo
  6. customtriturated with diethyl ester
  7. filtrationThe precipitate is collected by filtration
  8. customrecrystallised

Sources & evidence

ORD record
ord-989baddc55c440cc9d5ac6c47731cd40
Source dataset
uspto-grants-2015_06
Patent number
US09061973B2

Reaction notes

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