Sodium Hydroxide → 8-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 1758781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758781
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[C:10]([CH3:27])([CH3:26])[N:9]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]3[C:22]([CH3:25])=[N:23][N:24]=[C:11]3[C:10]([CH3:27])([CH3:26])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 205085396-(o-fluorophenyl)-1,4,4-trimethyl-8-nitro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Produkt 1

HCID 205085588-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

43.6 g (0.12 mol) of 6-(o-fluorophenyl)-1,4,4-trimethyl-8-nitro-4H-s-triazolo[4,3-a][1,4]benzodiazepine in 600 ml of concentrated hydrochloric acid are treated portionwise with a total of 80.55 g (0.36 mol) of tin chloride in such a manner that the temperature of the mixture does not exceed 85° C. Subsequently, the mixture is stirred at room temperature for 1 hour, cooled to 0° C. and cautiously neutralised with 900 ml of 10 N sodium hydroxide. After extracting the remaining suspension three times with methylene chloride, the combined organic phases are washed with saturated sodium chloride solution, dried and evaporated. Recrystallisation of the residue from 350 ml of ethanol at -30° C. gives 8-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 294° C.

Aufarbeitung

  1. customdoes not exceed 85° C
  2. temperaturecooled to 0° C.
  3. extractionAfter extracting the remaining suspension three times with methylene chloride
  4. washthe combined organic phases are washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customRecrystallisation of the residue from 350 ml of ethanol at -30° C.

Quellen und Nachweise

ORD-Eintrag
ord-c8980772c9734e4c859d797f6929f8bd
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374773

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