2,6-Dimethylaniline → HCID 178425630, compound

HRID 925014Notes

Reaction equation

HRID 925014 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C([Li])CCC.[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>O>[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]([NH:4][C:3]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:2]=2[CH3:1])=[NH:21])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 68962,6-DimethylanilineHCID 7724p-TolunitrileHCID 178418339Butyllithium

Product 1

HCID 178425630HCID 178425630, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts: 6.15 mL of 2,6-dimethylaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.86 g of 4-methylbenzonitrile (50.0 mmol). After refluxing overnight, the solution was deep red. Addition of water yielded a yellow solution with suspended solid. Solution was filtered, taken to dryness, resuspended in 100 mL of pentane and stirred vigorously for 1 hour. The resulting white solid was filtered, washed with 10 mL of pentane and dried in vacuo yielding 11.19 g (90%) of white powder. 1H NMR (400 MHz, CDCl3): 7.83 (d, 2H), 7.26 (d, 2H), 7.05 (d, 2H), 6.89 (t, 1H), 4.54 (s, 2H), 2.42 (s, 3H), 2.15 (s, 6H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a yellow solution
  3. filtrationSolution was filtered
  4. filtrationThe resulting white solid was filtered
  5. washwashed with 10 mL of pentane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e0fcd318d41a4687b14855f9bc34e401
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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