Benzene → N-((1-(6-((2,6-Diisopropylphenylimino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

HRID 2370668Notes

Reaction equation

HRID 2370668 reaction equation
C1C=CC=CC=1.[C:7]1([CH3:35])[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[NH:15][CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]=1[C:27]1[N:32]=[C:31]([CH:33]=O)[CH:30]=[CH:29][CH:28]=1.[CH:36]([C:39]1[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]([CH3:48])[CH3:47])[C:40]=1[NH2:41])([CH3:38])[CH3:37].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH:46]([C:42]1[CH:43]=[CH:44][CH:45]=[C:39]([CH:36]([CH3:38])[CH3:37])[C:40]=1[N:41]=[CH:33][C:31]1[N:32]=[C:27]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:25]=[CH:26][C:17]=2[CH2:16][NH:15][C:8]2[C:7]([CH3:35])=[CH:12][C:11]([CH3:13])=[CH:10][C:9]=2[CH3:14])[CH:28]=[CH:29][CH:30]=1)([CH3:48])[CH3:47]

Participants

6

Reactant 4

HCID 241BenzeneHCID 32484DiisopropylanilineHCID 521998p-Toluenesulfonic acid monohydrateHCID 866601036-{2-[(Mesitylamino)methyl]-1-naphthyl}pyridine-2-carbaldehyde

Product 1

HCID 68003896N-((1-(6-((2,6-Diisopropylphenylimino)methyl)pyridin-2-yl)naphthalen-2-yl)methyl)-2,4,6-trimethylaniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

Benzene (200 mL) was added to compound 5b (6.69 g, 17.6 mmol), and 2,6-diisopropylaniline (3.12 g, 17.6 mmol), and p-toluenesulfonic acid monohydrate (5 mg) in a 500 mL round-bottomed flask fitted with a Dean-Stark trap. The mixture was heated to reflux under nitrogen. After 2 hours, 1H NMR spectroscopy of an aliquot indicated that the reaction had proceeded to around 90% completion. All but about 50 mL of the benzene was removed by distillation and toluene (200 mL) was added. The mixture was heated to reflux and most of the toluene was removed by distillation. Drying of the residue under reduced pressure afforded a dirty yellow solid. Dissolution of the solid in warm Et2O, followed by filtration and cooling to −20° C. afforded 6b as nice yellow crystals. Yield from two crops: 6.5 g, 69%. 1H NMR (500 MHz, CD2Cl2): 8.36 (d, 1H), 8.33 (s, 1H), 7.97 (t, 1H), 7.93 (d, 2H), 7.59 (d, 1H), 7.39-7.51 (m, 4H), 7.17 (d, 2H), 7.10 (m, 1H), 6.72 (s, 2H), 4.01 (br d, 1H), 3.92 (d, 1H), 3.39 (br, 1H), 3.03 (sept, 2H), 2.18 (s, 3H), 2.03 (s, 6H), 1.18 (d, 12H).

Workup

  1. customfitted with a Dean-Stark trap
  2. temperatureThe mixture was heated
  3. temperatureto reflux under nitrogen
  4. customAll but about 50 mL of the benzene was removed by distillation and toluene (200 mL)
  5. additionwas added
  6. temperatureThe mixture was heated
  7. temperatureto reflux and most of the toluene
  8. customwas removed by distillation
  9. customDrying of the residue under reduced pressure
  10. customafforded a dirty yellow solid
  11. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-f12531b9a0f9446f89de5918fa80baf1
Source dataset
uspto-grants-2014_04
Patent number
US08710163B2

Reaction notes

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