Dimethyl Sulfoxide → HCID 20221292, compound

HRID 980975Notes

Reaction equation

HRID 980975 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.CS(C)=O.[OH-].[K+].[CH2:24](OS(OCC)(=O)=O)[CH3:25]>C1(C)C=CC=CC=1>[CH2:24]([N:9]([CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[CH3:25]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6163Diethyl SulfateHCID 14797Potassium HydroxideHCID 6486836(4-Methoxy-phenyl)-(2-pyridin-2-yl-ethyl)-amine

Product 1

HCID 20221292HCID 20221292, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

With stirring, 10.6 g (0.044 mole) of N-[2-(2-pyridyl)ethyl]-4-methoxyaniline, prepared in a manner similar to that described in Example 1, part A, was added to 25.0 ml of dimethylsulfoxide. After the solution was complete, 4.9 g of ground potassium hydroxide was added slowly to the solution maintaining a temperature under 40° C. After approximately one hour, 13.6 g (0.088 mole) of diethylsulfate was added dropwise to the reaction mixture while maintaining a temperature in the range of 25° to 40° C., and the resultant mixture was stirred for approximately eighteen hours at ambient temperature. To the reaction mixture, there was added 50.0 ml of toluene with stirring. The insoluble potassium sulfate was collected by filtration and discarded. The toluene solution was washed several times with saturated aqueous sodium chloride solution and dried with anhydrous sodium sulfate. The toluene was removed under reduced pressure to obtain 5.5 g of N-ethyl-N-[2-(2-pyridyl)ethyl]-4-methoxyaniline (Formula VI: R1 =C 2 H5 ; R2 =R9 =H; R11 =CH3O), a brown-colored oil. A significant infrared maximum appeared at 1592 cm-1 (C=C;s). The nuclear magnetic resonance spectrum was consistent with the assigned structure.

Workup

  1. temperaturewhile maintaining a temperature in the range of 25° to 40° C.
  2. stirringwith stirring
  3. filtrationThe insoluble potassium sulfate was collected by filtration
  4. washThe toluene solution was washed several times with saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe toluene was removed under reduced pressure

Sources & evidence

ORD record
ord-b01e51e37edf4c9f88ca10b9bc10e089
Source dataset
uspto-grants-1987_01
Patent number
US04639750

Reaction notes

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