Aniline → HCID 178425627, compound

HRID 925020Notes

Reaction equation

HRID 925020 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH3:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>O>[CH3:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[NH:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 7724p-TolunitrileHCID 178418339Butyllithium

Product 1

HCID 178425627HCID 178425627, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts: 4.60 mL of aniline (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 orange. Addition of water yielded a yellow solution with suspended solid. Solution was filtered and taken to dryness. The residue was treated with 50 mL of pentane, stirred for 30 minutes, and filtered yielding 8.23 g (78%) of light yellow solid. 1H NMR (400 MHz, CDCl3): 7.76 (d, 2H), 7.36 (t, 2H), 7.25 (d, 2H), 7.06 (t, 1H), 6.98 (d, 2 H), 4.79 (s, 2H), 2.40 (s, 3H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded a yellow solution
  3. filtrationSolution was filtered
  4. additionThe residue was treated with 50 mL of pentane
  5. filtrationfiltered
  6. customyielding 8.23 g (78%) of light yellow solid

Sources & evidence

ORD record
ord-3224d074540040708c0a7f340bef53c9
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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