Sulfuric Acid → 7-dimethylamino-6,7-dihydro [5H] benzocycloheptene

HRID 372541ノート

反応式

HRID 372541 の反応式
S(=O)(=O)(O)O.[CH3:6][N:7]([CH3:20])[CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[CH:10](O)[CH2:9]1.[OH-].[NH4+].[Cl-].[Na+]>O1CCOCC1>[CH3:6][N:7]([CH3:20])[CH:8]1[CH:9]=[CH:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH2:13][CH2:14]1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 203844387-dimethylamino-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene

生成物 1

HCID 30468617-dimethylamino-6,7-dihydro [5H] benzocycloheptene収率 49.3%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

実験手順

16 ml of 18 N sulfuric acid were added to a refluxing mixture of 8 g of 7-dimethylamino-5-hydroxy-6,7,8,9-tetrahydro [5H] benzocycloheptene and 80 ml of dioxane and after one half hour of reflux, another 80 ml of dioxane were added thereto. The mixture was refluxed another 30 minutes and was then cooled. The pH was raised above 10 by addition of concentrated ammonium hydroxide and the mixture was saturated with sodium chloride and was extracted with ethyl acetate. The organic extracts were washed with aqueous sodium chloride and then were dried and evaporated to dryness. The residue was chromatographed over silica gel and was eluted with a 7-3-1 cyclohexane-ethyl acetate-triethylamine mixture to obtain 3.6 g of 7-dimethylamino-6,7-dihydro [5H] benzocycloheptene.

後処理

  1. temperatureof reflux
  2. temperatureThe mixture was refluxed another 30 minutes
  3. temperaturewas then cooled
  4. extractionwas extracted with ethyl acetate
  5. washThe organic extracts were washed with aqueous sodium chloride
  6. customwere dried
  7. customevaporated to dryness
  8. customThe residue was chromatographed over silica gel
  9. washwas eluted with a 7-3-1 cyclohexane-ethyl acetate-triethylamine mixture

出典と根拠

ORDレコード
ord-5f83c836beed4d1488aaeefbff9e6ff2
出典データセット
uspto-grants-1978_05
特許番号
US04091115

反応ノート

読み込み中…