Hydrogen Bromide → alpha-Hydroxyalprazolam

HRID 267224

反応式

HRID 267224 の反応式
C([O:8][CH2:9][C:10]1[N:14]2[C:15]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:16]=3[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:18][CH2:19][C:13]2=[N:12][N:11]=1)C1C=CC=CC=1.Br.[OH-].[Na+].O>C(O)(=O)C.C(Cl)Cl>[C:20]1([C:17]2[C:16]3[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:15]=3[N:14]3[C:10]([CH2:9][OH:8])=[N:11][N:12]=[C:13]3[CH2:19][N:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

7

反応物 4

HCID 260Hydrogen BromideHCID 962WaterHCID 14798Sodium HydroxideHCID 204730831-(benzyloxymethyl)-6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

生成物 1

HCID 162244alpha-Hydroxyalprazolam

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

An amount of 25 g of 1-(benzyloxymethyl)-6-phenyl- 8-chloro-4H-s-triazolo[4,3-a] [1,4]benzodiazepine is dissolved in 200 ml of glacial acetic acid; there is then added to the solution 170 ml of 48% aqueous hydrobromic acid. The mixture is heated for 90 minutes at 80° and then cooled to 5°; while stirring is maintained, the mixture is adjusted to pH 6 with concentrated sodium hydroxide solution, and water as well as methylene chloride subsequently added. The organic phase is separated, washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated by evaporation. The residue is dissolved in ethyl acetate/methanol (9:1); the solution is filtered through a column of 150 g of silica gel (Merck, particle size 0.05 - 0.2 mm), and the column eluted with ethyl acetate/methanol (9:1) to (7:3). The eluate is concentrated by evaporation and the residue crystallised from ethyl acetate/ether to obtain 6-phenyl-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine-1-methanol, M.P. 210°-211°.

後処理

  1. temperatureThe mixture is heated for 90 minutes at 80°
  2. temperaturecooled to 5°
  3. temperatureis maintained
  4. additionsubsequently added
  5. customThe organic phase is separated
  6. washwashed with saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation
  9. dissolutionThe residue is dissolved in ethyl acetate/methanol (9:1)
  10. filtrationthe solution is filtered through a column of 150 g of silica gel (Merck, particle size 0.05 - 0.2 mm)
  11. washthe column eluted with ethyl acetate/methanol (9:1) to (7:3)
  12. concentrationThe eluate is concentrated by evaporation
  13. customthe residue crystallised from ethyl acetate/ether

出典と根拠

ORDレコード
ord-371e4044eee94e0d84a1b04546d397dd
出典データセット
uspto-grants-1976_03
特許番号
US03941799

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