N,N,2-Trimethylaniline → HCID 178506851, compound

HRID 1438894Notes

Reaction equation

HRID 1438894 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[C:4]([CH3:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.C([Li:15])CCC>CCCCCC>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][Li:15]

Participants

4

Reactant 2

HCID 11869N,N,2-TrimethylanilineHCID 178418339Butyllithium

Product 1

HCID 178506851HCID 178506851, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 96.0 g of N,N-dimethyl-o-toluidine and 444 ml of a 1.6 M solution of butyllithium in hexane was stirred for two days. Stirring was stopped and the orange solution was cooled in ice until it became cloudy, whereupon stirring was resumed with continuing cooling. A yellow solid separated. Volatile materials were removed, about 50 ml of ethyl ether was added, and the solution was stirred for another 24 hours. During this time a large amount of solid separated. It was washed from the flask with pentane to give 2-dimethylaminobenzyllithium in 100% yield (mp above 200° C with decomposition). The infrared absorption spectrum of the product was in agreement with its assigned structure.

Workup

  1. stirringStirring
  2. temperaturethe orange solution was cooled in ice until it
  3. stirringwhereupon stirring
  4. temperaturewith continuing cooling
  5. customA yellow solid separated
  6. customVolatile materials were removed
  7. additionabout 50 ml of ethyl ether was added
  8. stirringthe solution was stirred for another 24 hours
  9. customDuring this time a large amount of solid separated
  10. washIt was washed from the flask with pentane

Sources & evidence

ORD record
ord-b414de24dc63420088739ba4802439b3
Source dataset
uspto-grants-1977_11
Patent number
US04057565

Reaction notes

Loading…