Pyridine → 2-Heptyl-6-(5-cyano-2-pyrimidinyl)naphthalene

HRID 1381062Notes

Reaction equation

HRID 1381062 reaction equation
Cl.[CH2:2]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([C:19]([NH2:21])=[NH:20])[CH:13]=[CH:12]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:22](N(CC)CC)C.[N:29]1[CH:34]=[CH:33][CH:32]=CC=1>O>[CH2:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]3[N:21]=[CH:22][C:33]([C:34]#[N:29])=[CH:32][N:20]=3)[CH:15]=2)[CH:10]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 23323276HCID 23323276, compound

Product 1

HCID 135313302-Heptyl-6-(5-cyano-2-pyrimidinyl)naphthaleneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Heptyl-2-naphthalenecarboxamidine hydrochloride (4.0 g, 13 mmols), α-cyano-β-dimethylaminoacrolein (1.6 g, 13 mmols), triethylamine (30 ml) and pyridine (30 ml) were placed in a flask, followed by heating under reflux with stirring for 6 hours, cooling down to room temperature, and pouring the reaction mixture into water (500 ml) to deposit white solids, which were then separated by filtration and dissolved in toluene (100 ml), followed by washing the toluene layer with water, drying over anhydrous sodium sulfate and distilling off toluene under reduced pressure to obtain solids, which were recrystallized from a mixed solvent of ethanol-ethyl acetate (1:1) to obtain the objective 2-heptyl-6-(5-cyano-2-pyrimidinyl)naphthalene (3.0 g, 9.2 mmols) (yield: 70%). This product exhibited a liquid crystalline phase, and its crystalline-smectic phase transition point (C-S point) was 124.6°-125.6° C.; its smectic-nematic phase transition point (S-N point), 153.9°-154.1° C.; and its nematic-isotropic phase transition point (N-I point), 163.5°-163.7° C.

Workup

  1. temperatureby heating
  2. temperatureunder reflux
  3. customwere then separated by filtration
  4. dissolutiondissolved in toluene (100 ml)
  5. washby washing the toluene layer with water
  6. dry with materialdrying over anhydrous sodium sulfate
  7. distillationdistilling off toluene under reduced pressure
  8. customto obtain solids, which
  9. customwere recrystallized from a mixed solvent of ethanol-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-487d1c24d68144108408aa517d61bc43
Source dataset
uspto-grants-1986_04
Patent number
US04585575

Reaction notes

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