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

HRID 1762709

반응식

HRID 1762709 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 21218Trioctylmethylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69d871d00da848548497f3689c011320
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833245

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