Hydrochloric Acid → 9-chloro-2-methyl-7-phenyl-5H[1,2,4]triazolo-[5,1-a] [2,4]benzodiazepine

HRID 616908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 616908
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]1=[N:11][C:12]([CH3:14])=[N:13][N:6]1[C:5]2([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH2:15].[CH2:22]1N2CN3CN(C2)CN1C3.Cl>COCCOC>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7]3=[N:11][C:12]([CH3:14])=[N:13][N:6]3[CH2:22][N:15]=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric Acid2×HCID 4101Hexamethylenetetramine2×HCID 124680237-Chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]isoindol-5-amine

Produkt 1

HCID 124680259-chloro-2-methyl-7-phenyl-5H[1,2,4]triazolo-[5,1-a] [2,4]benzodiazepineAusbeute 40,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

To a stirring solution of 3.1 g (10.4 mmol) of 7-chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]-isoindol-5-amine and 3.1 g (22 mmol) of hexamethylenetetramine (hexamine) in 75 ml of DME is added 1.5 ml of 4 N HCl (dioxane). A precipitate forms immediately and the two phase mixture is refluxed. After 5 hours another 1.0 g of hexamine is added and reflux is continued overnight. An additional 1.5 ml of the HCl solution is added after 12 hours and again after an additional 24 hours. After another 24 hours, thin layer chromatography (TLC) shows the disappearance of starting material. The mixture is filtered and the solvent is removed from the filtrate under vacuum. The residue is taken up in CHCl3 and applied to a 5×10 cm silica gel column (Baker 60-200 mesh). The column is eluted with CHC13 until all of the high Rf material (followed by TLC) is recovered. The solvent is removed in vacuo and the residue recrystallized from 20 ml of acetonitrile to yield 1.3 g of pure product: m.p. 150.5°-152° [concentration of the mother liquor gives an additional 0.2 g for a total yield of 1.5 g (46.6%)].

Aufarbeitung

  1. temperatureA precipitate forms immediately and the two phase mixture is refluxed
  2. temperaturereflux
  3. waitAfter another 24 hours
  4. filtrationThe mixture is filtered
  5. customthe solvent is removed from the filtrate under vacuum
  6. washThe column is eluted with CHC13 until all of the high Rf material (followed by TLC)
  7. customis recovered
  8. customThe solvent is removed in vacuo
  9. customthe residue recrystallized from 20 ml of acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-b362991737ce4fbcbb7df3a5a34cb890
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04076823

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