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Methanol → 2-chloro-6,11-dihydro-5H-dibenz[b,e]azepine

HRID 355864
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HRID 355864 반응식
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][C:7](=O)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10](=O)[C:4]=2[CH:3]=1.[B].CSC.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]2[NH:6][CH2:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[CH2:10][C:4]=2[CH:3]=1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 134665322-Chloro-5H-dibenzo[b,e]azepine-6,11-dione

생성물 1

HCID 537916382-chloro-6,11-dihydro-5H-dibenz[b,e]azepine수율 64.1%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a mixture of 7.28 g of 2-chloro-5H-dibenz[b,e]azepine-6,11-dione in 25 ml of anhydrous tetrahydrofuran, under argon, is added dropwise 8.5 ml of (10M) boron-dimethyl sulfide. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is heated at reflux for 3 hours and cooled to room temperature. While stirring, 25 ml of methyl alcohol is carefully added, followed by 100 ml of 2N NaOH. The reaction mixture is heated at reflux for 24 hours and the solid collected. The solid is dissolved in methylene chloride and washed with 2N citric acid, water and dried (Na2SO4). The volatiles are evaporated in vacuo to give 4.16 g of a residue which is crystallized from ethyl acetate-hexane to give 2.05 g of the desired product as a crystalline solid, m.p. 137°-141° C.

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled to room temperature
  4. stirringWhile stirring
  5. temperatureThe reaction mixture is heated
  6. temperatureat reflux for 24 hours
  7. customthe solid collected
  8. dissolutionThe solid is dissolved in methylene chloride
  9. washwashed with 2N citric acid, water
  10. dry with materialdried (Na2SO4)
  11. customThe volatiles are evaporated in vacuo

출처 및 근거

ORD 기록
ord-909e70af6e044c61bf44a00786b6e9ea
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05834461

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