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

HRID 362361
ノート
印刷プレビュー

反応式

HRID 362361 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-af4c20ece5004fdd8097d8f9267aeb5c
出典データセット
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05869483

反応ノート

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