4-tert-Butylbenzonitrile → HCID 178440935, compound

HRID 925018

Reaction equation

HRID 925018 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.[C:17]([C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>O>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[C:1]([CH3:4])([CH3:2])[CH3:3])=[NH:26])=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 778834-tert-ButylbenzonitrileHCID 805742-tert-ButylanilineHCID 178418339Butyllithium

Product 1

HCID 178440935HCID 178440935, compound

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), 8.50 ml of 4-t-butylbenzonitrile (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 for 30 minutes, and filtered yielding 13.43 g (87%) of light orange solid. 1H NMR (400 MHz, CDCl3): 7.87 (d, 2H), 7.49 (d, 2H), 7.41 (d, 1H), 7.17 (t, 1H), 7.00 (t, 1H), 6.81 (d, 1 H), 4.75 (s, 2H), 1.41 (s, 9H), 1.36 (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
  6. customyielding 13.43 g (87%) of light orange solid

Sources & evidence

ORD record
ord-786f35efc25a4ec3bdef2f03e83e14d1
Source dataset
uspto-grants-2016_03
Patent number
US09283555B2

Linked notes

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