Methyl iodide → HCID 66916764, compound

HRID 1879237Notes

Reaction equation

HRID 1879237 reaction equation
[CH2:1]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[CH2:17]([Li])CCC.IC>C(OCC)C.CCCCCC>[CH2:1]([N:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 775228HCID 775228, compoundHCID 178418339Butyllithium

Product 1

HCID 66916764HCID 66916764, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

5.15 g of N-(3-Anisyl)-N-phenyl-amine were dissolved in 25.0 ml of anhydrous diethylether. 11.0 g of a 2.50 M solution of n-butyl lithium in n-hexane was added with stirring. After completion of the addition the reaction mixture was heated to reflux for 30 min 3.90 g of iodomethane are added and the reaction mixture was heated to reflux for additional 4 hours. After extraction with 2.00 N sodium hydroxide solution (three times) the organic layer was dried with anhydrous sodium sulfate. After filtration the solvent was removed in vacuo and the crude product purified by fractionated distillation in vacuo. At a temperature of 70-90° C./0.01 mbar 2.40 g (45.0%) of APMA was collected as yellow liquid.

Workup

  1. additionAfter completion of the addition the reaction mixture
  2. temperaturewas heated
  3. additionare added
  4. temperaturethe reaction mixture was heated
  5. temperatureto reflux for additional 4 hours
  6. extractionAfter extraction with 2.00 N sodium hydroxide solution (three times) the organic layer
  7. dry with materialwas dried with anhydrous sodium sulfate
  8. filtrationAfter filtration the solvent
  9. customwas removed in vacuo
  10. distillationthe crude product purified by fractionated distillation in vacuo
  11. customAt a temperature of 70-90° C./0.01 mbar 2.40 g (45.0%) of APMA was collected as yellow liquid

Sources & evidence

ORD record
ord-6b344a7c74064aa4b98dadaf9913363a
Source dataset
uspto-grants-2012_11
Patent number
US08314162B2

Reaction notes

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