p-Tolunitrile → HCID 178436103, compound

HRID 925019Notes

Reaction equation

HRID 925019 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5])[CH3:2].C([Li])CCC.[CH3:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>O>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:20](=[NH:21])[C:19]1[CH:22]=[CH:23][C:16]([CH3:15])=[CH:17][CH:18]=1)[CH3:2]

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 113572-EthylanilineHCID 178418339Butyllithium

Product 1

HCID 178436103HCID 178436103, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts: 6.18 mL of 2-ethylaniline (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 dark brown. Addition of water yielded a yellow solution with suspended solid. Solution was filtered and taken to dryness. The residue was treated with 75 mL of pentane, stirred overnight, and filtered yielding 10.51 g (88%) of light yellow solid. 1H NMR (400 MHz, CDCl3): 7.79 (d, 2H), 7.25 (d, 3H), 7.17 (t, 1H), 7.02 (t, 1H), 6.86 (d, 1 H), 4.68 (s, 2H), 2.57 (q, 2H), 2.41 (s, 3H), 1.17 (t, 3H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a yellow solution
  3. filtrationSolution was filtered
  4. additionThe residue was treated with 75 mL of pentane
  5. filtrationfiltered
  6. customyielding 10.51 g (88%) of light yellow solid

Sources & evidence

ORD record
ord-ba84f3ca8c47404ba4ea89900700b6ca
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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