Hydrogen Bromide → alpha-Hydroxytriazolam

HRID 267225

Reaktionsgleichung

Reaktionsgleichung von HRID 267225
Br.COC1C=CC(C[O:9][CH2:10][C:11]2[N:15]3[C:16]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:17]=4[C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])=[N:19][CH2:20][C:14]3=[N:13][N:12]=2)=CC=1.[OH-].[Na+]>C(O)(=O)C>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[C:17]2[CH:28]=[C:29]([Cl:32])[CH:30]=[CH:31][C:16]=2[N:15]2[C:11]([CH2:10][OH:9])=[N:12][N:13]=[C:14]2[CH2:20][N:19]=1

Komponenten

5

Edukt 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 204730851-[(p-methoxybenzyloxy)-methyl]-6-(o-chlorophenyl)-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Produkt 1

HCID 1963alpha-Hydroxytriazolam

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

An amount of 72 ml of 48% aqueous hydrobromic acid is added to 20° to a solution of 9.7 g of 1-[ (p-methoxybenzyloxy)-methyl]-6-(o-chlorophenyl)-8-chloro-4H-s-triazolo[4,3-a][1,4]benzodiazepine in 90 ml of glacial acetic acid. The reaction mixture is stirred for 55 minutes; it is then neutralised with 30% sodium hydroxide solution and extracted with methylene chloride. The organic phase is separated, washed with water, dried over sodium sulphate and concentrated by evaporation. Crystallisation of the residue from ethyl acetate/petroleum ether yields 6-(o-chlorophenyl)-8-chloro-4 h-s-triazolo[4,3-a] [1,4]benzodiazepine-1-methanol, M.P. 235°-237°.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. customThe organic phase is separated
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation
  6. customCrystallisation of the residue from ethyl acetate/petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-c916bc4dd7264334ac786fec36a6f8ea
Quelldatensatz
uspto-grants-1976_03
Patentnummer
US03941799

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