Acetohydrazide → Triazolam

HRID 649264ノート

反応式

HRID 649264 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=O)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.[H-].[Na+].[H-].[H][H].O1CCN(P(Cl)(N2CCOCC2)=O)CC1.[C:41]([NH:44][NH2:45])(=O)[CH3:42]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:41]([CH3:42])=[N:44][N:45]=[C:10]3[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

参加物

8

反応物 6

HCID 14039AcetohydrazideHCID 17925DelorazepamHCID 24758Sodium hydrideHCID 166653HydrideHCID 12506606Bis(morpholino)phosphinyl chlorideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 5556Triazolam

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 610 mg. (2 mmoles) of 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one in 10 ml. of dry tetrahydrofuran at room temperature was added 115 mg. of a 50% dispersion of sodium hydride in oil (2.4 mmoles of hydride). The mixture was warmed gently on the steam bath for approximately 1 hour until hydrogen evolution stopped. Dimorpholinophosphinic chloride (764 mg., 3.0 mmoles) was added and the resulting mixture was stirred at room temperature for 2 hours. To this mixture was then added a solution of 296 mg. (4 mmoles) of acethydrazide in 5 ml. of dry tetrahydrofuran and stirring was continued for 15 minutes at room temperature. Solvents were evaporated and the residue was dissolved in 20 ml. of butanol and heated to reflux for 2 hours. Butanol was evaporated. The residue was partitioned between methylene chloride and water. The methylene chloride layer was dried and evaporated. Crystallization of the residue from isopropanol-ether-petroleum ether yielded, in two crops, final product having a m.p. of 225°-227°.

後処理

  1. additionTo this mixture was then added a solution of 296 mg
  2. waitwas continued for 15 minutes at room temperature
  3. customSolvents were evaporated
  4. dissolutionthe residue was dissolved in 20 ml
  5. temperatureof butanol and heated
  6. temperatureto reflux for 2 hours
  7. customButanol was evaporated
  8. customThe residue was partitioned between methylene chloride and water
  9. dry with materialThe methylene chloride layer was dried
  10. customevaporated
  11. customCrystallization of the residue from isopropanol-ether-petroleum ether

出典と根拠

ORDレコード
ord-81ea9a22fdd84a6dbd5c76e1402448c5
出典データセット
uspto-grants-1988_04
特許番号
US04739049

反応ノート

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