Toluene → 2-Heptyl-6-(5-ethyl-2-pyrimidinyl)naphthalene

HRID 1381061ノート

反応式

HRID 1381061 の反応式
[OH-].[Na+].Cl.[CH2:4]([C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C:21]([NH2:23])=[NH:22])[CH:15]=[CH:14]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:24]1([CH3:30])[CH:29]=[CH:28]C=C[CH:25]=1>CO>[CH2:4]([C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]3[N:23]=[CH:30][C:24]([CH2:29][CH3:28])=[CH:25][N:22]=3)[CH:17]=2)[CH:12]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

5

反応物 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 23323276HCID 23323276、化合物

生成物 1

HCID 135313252-Heptyl-6-(5-ethyl-2-pyrimidinyl)naphthalene収率 60%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
60 °C

実験手順

NaOH (1.1 g, 26 mmols) was added to anhydrous methanol (40 ml) and dissolved therein by heating to 60° C. with stirring. To the solution was added 6-heptyl-2-naphthalenecarboxamidine hydrochloride (4.0 g, 13 mmols) to prepare a suspension with stirring. To this suspension was dropwise added over one minute a solution obtained by dissolving α-ethyl-β-dimethylaminoacrolein (1.7 g, 13 mmols) in anhydrous methanol (5 ml), followed by gently refluxing the mixture with stirring for 2 hours, distilling off methanol under the atmospheric pressure after completion of the reaction, adding toluene (50 ml) to the residue to extract the resulting product, washing the extraction solution with a 2N-NaOH aqueous solution and then with water, drying over anhydrous sodium sulfate, and distilling off toluene under reduced pressure to obtain solids, which were then recrystallized from ethanol to obtain the objective 2-heptyl-6-(5-ethyl-2-pyrimidinyl)naphthalene (2.5 g, 7.8 mmols) (yield: 60%). M.P.: 62.3°-63.1° C.

後処理

  1. dissolutiondissolved
  2. customto prepare a suspension
  3. stirringwith stirring
  4. additionTo this suspension was dropwise added over one minute a solution
  5. customobtained
  6. temperatureby gently refluxing the mixture
  7. stirringwith stirring for 2 hours
  8. distillationdistilling off methanol under the atmospheric pressure
  9. customafter completion of the reaction
  10. extractionto extract the resulting product
  11. washwashing the extraction solution with a 2N-NaOH aqueous solution
  12. dry with materialwith water, drying over anhydrous sodium sulfate
  13. distillationdistilling off toluene under reduced pressure
  14. customto obtain solids, which
  15. customwere then recrystallized from ethanol

出典と根拠

ORDレコード
ord-d593f3f4dc2447a4b3d428c7e9c53007
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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