N,N,N',N'-Tetramethylmethanediamine → HCID 18933594, compound

HRID 1598316Notes

Reaction equation

HRID 1598316 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][N:11]([CH2:13]N(C)C)[CH3:12]>O1CCOCC1>[CH3:10][N:11]([CH2:13][C:3]1[C:2]([OH:1])=[CH:9][CH:8]=[CH:7][C:4]=1[C:5]#[N:6])[CH3:12]

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 133943-Cyanophenol

Product 1

HCID 18933594HCID 18933594, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-hydroxybenzonitrile (20.0 g) and N,N,N',N'-tetramethyldiaminomethane (22.9 ml) in 1,4-dioxane (200 ml) was heated on a steam bath for 48 hours. The mixture was evaporated to dryness and the residue dissolved in 2M hydrochloric acid. The solution was washed with ethyl acetate and then the acidic layer was basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give an oil which was purified by column chromatography on silica to give 2-dimethylaminomethyl-3-hydroxybenzonitrile. The structure was confirmed by 1H NMR spectroscopy.

Workup

  1. temperaturewas heated on a steam bath for 48 hours
  2. customThe mixture was evaporated to dryness
  3. dissolutionthe residue dissolved in 2M hydrochloric acid
  4. washThe solution was washed with ethyl acetate
  5. extractionextracted with dichloromethane
  6. customto give an oil which
  7. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-450b8298cb374d1192f74b8546584de4
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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