HCID 86750154, compound → HCID 86750153, compound

HRID 233416Notes

Reaction equation

HRID 233416 reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][CH:6]1[OH:12])[CH3:3].[Li:13]CCCC>CCCCCC.C1(C)C=CC=CC=1>[CH3:3][N:2]([CH:4]=[C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][CH:6]1[O-:12])[CH3:1].[Li+:13]

Participants

5

Reactant 2

HCID 86750154HCID 86750154, compoundHCID 178418339Butyllithium

Product 1

HCID 86750153HCID 86750153, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

N,N-Dimethyl-2-aminomethylene-4-methylpheno1 (11.5 g, 57.8 mmol as 97.3% pure), was added slowly to n-BuLi (44 ml of a 1.6M solution in hexane, 70.25 mmol) in toluene (30 ml). A very exothermic reaction occurred and the mixture was cooled whilst addition was taking place. A clear straw coloured solution resulted, which was continually stirred until the temperature dropped to ambient. Solvent was next removed until a white precipitate formed. From which recrystallisation from hexane by refrigeration (12 h) caused large pyramidal crystals to form.

Workup

  1. customA very exothermic reaction
  2. temperaturethe mixture was cooled whilst addition
  3. customresulted
  4. additiondropped to ambient
  5. customSolvent was next removed until a white precipitate
  6. customformed
  7. customFrom which recrystallisation from hexane by refrigeration (12 h)
  8. customto form

Sources & evidence

ORD record
ord-9420e5bae7f0438cbd601d9b9cca64ee
Source dataset
uspto-grants-1997_01
Patent number
US05593464

Reaction notes

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