Potassium Carbonate → 2-Phenyl-4-(1-naphthyl)-5-methylimidazole

HRID 389229ノート

反応式

HRID 389229 の反応式
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:31])[C:19]([C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1)=O>O1CCCC1>[C:3]1([C:2]2[NH:9][C:18]([CH3:31])=[C:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 80289Benzamidine, hydrochlorideHCID 2311612-Bromo-1'-propionaphthone2 回

生成物 1

HCID 589916112-Phenyl-4-(1-naphthyl)-5-methylimidazole

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension consisting of 50.1 g (0.32 mol) of benzamidine hydrochloride, 133 g (0.96 mol) of potassium carbonate, and 250 mL of tetrahydrofuran was heated under reflux for one hour, and the foregoing toluene solution of 2-bromo-1′-propionaphthone was added dropwise over 50 minutes. After completion of addition, heated under reflux for 2 hours. Next, the reaction mixture was concentrated in vacuo, the resulting concentrate was diluted with 200 mL of toluene, and the solution was poured into 600 mL of water. The mixture was stirred to precipitate a solid. This solid was collected by filtration, successively washed with toluene and water, and then dried to obtain a crude crystal as a desired material. This crude crystal was recrystallized from DMF to obtain 48.1 g (yield: 52.9%) of a white powder.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for one hour
  3. additionAfter completion of addition
  4. temperatureheated
  5. temperatureunder reflux for 2 hours
  6. concentrationNext, the reaction mixture was concentrated in vacuo
  7. concentrationthe resulting concentrate
  8. additionwas diluted with 200 mL of toluene
  9. additionthe solution was poured into 600 mL of water
  10. customto precipitate a solid
  11. filtrationThis solid was collected by filtration
  12. washsuccessively washed with toluene and water
  13. customdried

出典と根拠

ORDレコード
ord-db98e58e9f0e439a8316faacd479ceaa
出典データセット
uspto-grants-2013_02
特許番号
US08378116B2

反応ノート

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