Methanol → 5,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

HRID 1420026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420026
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][C:9](=O)[CH2:10][C:4]2=[N:3][N:2]=1.B.CSC.CO>O1CCCC1>[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[NH:8][CH2:9][CH2:10][C:4]2=[N:3][N:2]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 218371285,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one

Produkt 1

HCID 218370045,6-Dihydro-4H-[1,2,4]triazolo[4,3-a][1,5]benzodiazepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 7.0 g of 5,6-dihydro-4H-[1,2,4]-triazolo-[4,3-a][1,5]benzodiazepin-5-one in 25 ml of tetrahydrofuran is added 9 ml of 10N borane-dimethylsulfide in tetrahydrofuran. The mixture is refluxed for 6 hours, cooled to room temperature and 25 ml of methanol added dropwise. The volatiles are removed under vacuum and to the residue is added 100 ml of 2N sodium hydroxide. The mixture is refluxed for 5 hours, chilled and extracted with dichloromethane. The extract is washed with 2N citric acid, water and dried (Na2SO4). The solvent is removed under vacuum to give a solid. The solid is purified by chromatography on silica gel to give the desired product.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 6 hours
  2. customThe volatiles are removed under vacuum and to the residue
  3. additionis added 100 ml of 2N sodium hydroxide
  4. temperatureThe mixture is refluxed for 5 hours
  5. temperaturechilled
  6. extractionextracted with dichloromethane
  7. washThe extract is washed with 2N citric acid, water
  8. dry with materialdried (Na2SO4)
  9. customThe solvent is removed under vacuum
  10. customto give a solid
  11. customThe solid is purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ce2b80bc37a64f688173d03ee362f36d
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889001

Notizen zur Reaktion

Wird geladen…