p-Tolunitrile → HCID 178425629, compound

HRID 925017Notes

Reaction equation

HRID 925017 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1>O>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH:7][C:22](=[NH:23])[C:21]1[CH:24]=[CH:25][C:18]([CH3:17])=[CH:19][CH:20]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7724p-TolunitrileHCID 805742-tert-ButylanilineHCID 178418339Butyllithium

Product 1

HCID 178425629HCID 178425629, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Procedure as described for Amidine I using the following amounts: 7.80 mL of 2-t-butylaniline (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 an orange 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 11.14 g (84%) of off-white material. 1H NMR (400 MHz, CDCl3): 7.82 (d, 2H), 7.41 (d, 1H), 7.27 (d, 2H), 7.17 (t, 1H), 7.00 (t, 1H), 6.82 (d, 1 H), 4.75 (s, 2H), 2.42 (s, 3H), 1.40 (s, 9H).

Workup

  1. temperatureAfter refluxing overnight
  2. customyielded an orange solution
  3. filtrationSolution was filtered
  4. additionThe residue was treated with 75 mL of pentane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d70594401e0f41e38b27f6204d006976
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Reaction notes

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