1,3-Dimethyl-2-imidazolidinone → HCID 66589436, compound

HRID 2098261Notes

Reaction equation

HRID 2098261 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]([CH3:7])[C:3]1=O.P(Cl)(Cl)([Cl:11])=O.[CH2:14]([N:16](CC)[CH2:17][CH3:18])[CH3:15].N1CCCC1>ClCCl.C1(C)C=CC=CC=1>[Cl-:11].[CH3:1][NH+:2]1[CH2:6][CH2:5][N:4]([CH3:7])[CH:3]1[N:16]1[CH2:17][CH2:18][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinone2×HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 31268Pyrrolidine

Product 1

HCID 66589436HCID 66589436, compoundYield 90.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
65 °C

Procedure

In a three-necked flask equipped with a dropping funnel and a reflux condenser were placed 19.4 g (170 millimoles) of 1,3-dimethyl-2-imidazolidinone and 50 mL of toluene in an atmosphere of nitrogen. Then, 13.0 g (85 millimoles) of phosphorus oxychloride was added and stirred at 65° C. Heating was stopped after 1 hour, the flask was cooled in an ice bath, and a solution containing the chlorination product of 1,3-dimethyl-2-imidazolidinone was obtained. To this solution were added 50 mL of dichloromethane and 23.6 mL (170 millimoles) of triethylamine in succession. To the resulting solution was added dropwise a solution of 13.8 mL (170 millimoles) of pyrrolidine in 50 mL of dichloromethane over a period of approximately 30 minutes while cooling the solution in an ice bath. Upon completion of the dropwise addition, the ice bath was removed and the solution was stirred at 55° C. The reaction mixture was cooled to room temperature after 1 hour, the insoluble matters were removed by filtration, and the filtrate was distilled off under reduced pressure. The residue was purified by column chromatography to give 15.9 g of 4,5-dihydro-1,3-dimethyl-2-(1-pyrrolidinyl)-1H-imidazolium chloride as a light yellow solid; this compound is a cyclic guanidine salt comprising the cation designated by chemical formula 1 and Cl− and is hereinafter referred to as cyclic guanidine salt 1. The solid showed a melting point of 49° C. and was hence a cyclic guanidine salt qualified for an ionic liquid.

Workup

  1. customIn a three-necked flask equipped with a dropping funnel and a reflux condenser
  2. temperatureHeating
  3. temperaturethe flask was cooled in an ice bath
  4. customwas obtained
  5. temperaturewhile cooling the solution in an ice bath
  6. additionUpon completion of the dropwise addition
  7. customthe ice bath was removed
  8. stirringthe solution was stirred at 55° C
  9. temperatureThe reaction mixture was cooled to room temperature after 1 hour
  10. customthe insoluble matters were removed by filtration
  11. distillationthe filtrate was distilled off under reduced pressure
  12. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9acc92c90c8e41948bf104bbceac2964
Source dataset
uspto-grants-2013_05
Patent number
US08450478B2

Reaction notes

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