Methyl iodide → HCID 19097131, compound

HRID 486005Notes

Reaction equation

HRID 486005 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[O:15][CH3:16])#[N:2].IC.[CH2:19](N(CC)CC)C>C(O)C.O>[C:1]([CH2:3][CH2:4][CH2:5][N:6]([CH3:19])[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[O:15][CH3:16])#[N:2]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 8471TriethylamineHCID 19097125HCID 19097125, compound

Product 1

HCID 19097131HCID 19097131, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-(3-cyanopropyl)-2,5-dimethoxyaniline (46.2 g; 0.22 mol) in absolute ethanol (400 ml) were added iodomethane (47.7 g; 0.34 mol) and triethylamine (34.0 g; 0.34 mol). After stirring at 50° C. for 24 hours a further portion of iodomethane (47.7 g; 0.34 mol) was added to the reaction mixture, which was then heated at 50° C. for a further 24 hours. The reaction mixture was then cooled, diluted with water (500 ml) and extracted with dichloromethane (3×200 ml) and washed with water (2×400 ml). The resulting organic extract was dried (MgSO4), the solvent was then removed under reduced pressure to give a brown oil. The crude product was purified by flash chromatography, eluting first with hexane and subsequently increasing the polarity with dichloromethane. This procedure afforded the product as a colourless oil (26.8 g; 54%).

Workup

  1. additionwas added to the reaction mixture, which
  2. temperatureThe reaction mixture was then cooled
  3. extractionextracted with dichloromethane (3×200 ml)
  4. washwashed with water (2×400 ml)
  5. extractionThe resulting organic extract
  6. dry with materialwas dried (MgSO4)
  7. customthe solvent was then removed under reduced pressure
  8. customto give a brown oil
  9. customThe crude product was purified by flash chromatography
  10. washeluting first with hexane
  11. temperaturesubsequently increasing the polarity with dichloromethane

Sources & evidence

ORD record
ord-b94485a235544712855e99c36da90ebd
Source dataset
uspto-grants-1994_03
Patent number
US05290630

Reaction notes

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