Sodium Hydroxide → (+/-)-8-Methyl-5-(4-nitrophenyl)-7-(2-pyrimidinyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25087
S(O[CH:6]([CH3:35])[CH2:7][C:8]1[C:16]([C:17]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[N:18][NH:19][C:20]2[N:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:15][C:11]2[O:12][CH2:13][O:14][C:10]=2[CH:9]=1)(=O)(=O)C.[OH-].[Na+]>ClCCl.CO>[CH3:35][CH:6]1[CH2:7][C:8]2[CH:9]=[C:10]3[O:14][CH2:13][O:12][C:11]3=[CH:15][C:16]=2[C:17]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=2)=[N:18][N:19]1[C:20]1[N:25]=[CH:24][CH:23]=[CH:22][N:21]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 1317247421-{6-[(4-Nitrophenyl)-(pyrimidin-2-yl-hydrazono)-methyl]-benzo-1,3-dioxol-5-yl}-propan-2-ol mesylate

Produkt 1

HCID 22565487(+/-)-8-Methyl-5-(4-nitrophenyl)-7-(2-pyrimidinyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepineAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A mixture of 3.13 g (6.27 mmol) of the compound obtained in Step B, 60 ml of a 1:1 mixture of dichloromethane-methanol and 0.52 ml (6.90 mmol) of 50% sodium hydroxide solution was stirred at room for 1.5 h. After filtration the reaction mixture was concentrated, the residue was treated with water and recrystallized from three fold dimethylformamide containing 10% water to yield 1.96 g (77%) of the title compound; Mp.: 261-263° C.

Aufarbeitung

  1. filtrationAfter filtration the reaction mixture
  2. concentrationwas concentrated
  3. additionthe residue was treated with water
  4. customrecrystallized from three fold dimethylformamide containing 10% water

Quellen und Nachweise

ORD-Eintrag
ord-c641818e40aa43a2ac61a768a117d1fa
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858605B2

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