N,N,N',N'-Tetramethylethylenediamine → HCID 10445976, compound

HRID 1463426Notes

Reaction equation

HRID 1463426 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([CH3:10])[C:3]=1[O:11][CH3:12].CN(C)CCN(C)C.C([Li])CCC.[CH:26](=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1>CCOCC.CCCCCC.O>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([CH:26]([OH:33])[C:5]2[C:4]([CH3:10])=[C:3]([O:11][CH3:12])[C:2]([CH3:1])=[CH:7][C:6]=2[O:8][CH3:9])[CH:28]=1

Participants

8

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 103713-PyridinecarboxaldehydeHCID 6433742,5-dimethoxy-1,3-dimethylbenzeneHCID 178418339Butyllithium

Product 1

HCID 10445976HCID 10445976, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-65 °C

Procedure

3.0 g of 1,3-dimethyl-2,5-dimethoxybenzene and 3.1 g of tetramethylethylenediamine were dissolved in 30 ml of dry ether and 17 ml of a 1.6M solution of n-butyllithium in hexane was added dropwise thereto in a nitrogen atmosphere at room temperature. After 1 hour, the mixture was cooled to -65° C. and a solution of 2.9 g of nicotinaldehyde in 10 ml of ether was added thereto. After 30 minutes, the reaction was ceased by adding water and the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. After distilling off the solvent, 6.4 g of a crude product of the title compound was obtained.

Workup

  1. customat room temperature
  2. waitAfter 30 minutes
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationAfter distilling off the solvent, 6.4 g of a crude product of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-e6436a7a63314dceae549fd502051099
Source dataset
uspto-grants-1994_04
Patent number
US05300518

Reaction notes

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