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

HRID 1381062ノート

反応式

HRID 1381062 の反応式
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]

参加物

5

反応物 3

HCID 1049PyridineHCID 8471TriethylamineHCID 23323276HCID 23323276、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-487d1c24d68144108408aa517d61bc43
出典データセット
uspto-grants-1986_04
特許番号
US04585575

反応ノート

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