Benzene → 5,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

HRID 35172ノート

反応式

HRID 35172 の反応式
[OH-].[Na+].[N:3]#[C:4][NH2:5].C1C=CC=CC=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]Br>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[CH:16]1[C:15]2[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH2:26][N:3]([C:4]#[N:5])[CH2:13][C:14]=2[CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 241BenzeneHCID 9864CyanamideHCID 14798Sodium HydroxideHCID 2519622,2'-Bis(bromomethyl)-1,1'-biphenyl

生成物 1

HCID 198338865,7-dihydro-6H-dibenz[c,e]azepine-6carbonitrile

試薬・触媒・溶媒 2

HCID 21218Trioctylmethylammonium chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

180 ml of 50% sodium hydroxide solution are treated at about 60° C. in sequence with 7.7 g of cyanamide, 1.3 g of tricaprylmethylammonium chloride, 360 ml of benzene and 62 g of 2,2'-bis(bromomethyl)-biphenyl, and the mixture is stirred at 60°-70° C. for 6 hours. After cooling the reaction mixture this is transferred to a separating funnel and shaken with 50 ml of methylene chloride, whereby the separated product is taken up in the methylene chloride phase. The aqueous phase is back-extracted twice with methylene chloride. The combined extracts are subsequently washed with water, dried over anhydrous sodium sulphate and evaporated, and the residue is taken up in 100 ml of toluene and the solution is heated to reflux temperature, filtered and treated at about 50° C. with 200 ml of tert.-butyl methyl ether. Finally, the crystals which are precipitated by ice-cooling are filtered off under suction and dried. In this manner there is obtained pure 5,7-dihydro-6H-dibenz[c,e]azepine-6-carbonitrile, m.p. 121°-124° C.

後処理

  1. temperatureAfter cooling the reaction mixture
  2. customthis is transferred to a separating funnel
  3. extractionThe aqueous phase is back-extracted twice with methylene chloride
  4. washThe combined extracts are subsequently washed with water
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. temperaturethe solution is heated
  8. temperatureto reflux temperature
  9. filtrationfiltered
  10. additiontreated at about 50° C. with 200 ml of tert.-butyl methyl ether
  11. customFinally, the crystals which are precipitated by ice-
  12. temperaturecooling
  13. filtrationare filtered off under suction
  14. customdried

出典と根拠

ORDレコード
ord-11b628a4b27f423281a6d5ad398d6874
出典データセット
uspto-grants-1988_08
特許番号
US04766115

反応ノート

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