Reaktion #53345

ord-3be6871f10994b319dc9c569ce143a0a

Reaktionsgleichung

CC1Cc2cc3c(cc2C(c2ccc([N+](=O)[O-])cc2)=NN1C(N)=S)OCO3
starting material I
CC1Cc2cc3c(cc2C(c2ccc([N+](=O)[O-])cc2)=NN1C(N)=S)OCO3
(±)-8-Methyl-5-(4-nitrophenyl)-7-thiocarbamoyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
CCOC(=O)C(=O)CBr
ethyl bromopyruvate
→
CCOC(=O)c1csc(N2N=C(c3ccc([N+](=O)[O-])cc3)c3cc4c(cc3CC2C)OCO4)n1
title compound
Ausbeute 85.0%
CCOC(=O)c1csc(N2N=C(c3ccc([N+](=O)[O-])cc3)c3cc4c(cc3CC2C)OCO4)n1
(±)-7-(4-Ethoxycarbonyl-thiazol-2-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
Ausbeute 85.0%

Edukte

CC1Cc2cc3c(cc2C(c2ccc([N+](=O)[O-])cc2)=NN1C(N)=S)OCO3
starting material I
CC1Cc2cc3c(cc2C(c2ccc([N+](=O)[O-])cc2)=NN1C(N)=S)OCO3
(±)-8-Methyl-5-(4-nitrophenyl)-7-thiocarbamoyl-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine
CCOC(=O)C(=O)CBr
ethyl bromopyruvate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling the precipitated crystals
  2. 2
    Filtrationwere filtered off
  3. 3
    Waschenwashed with ethanol
  4. 4
    Sonstigedried

Vorschrift

A mixture of 0.45 g (1.17 mmol) of the starting material I, 0.46 g (2.36 mmol) of ethyl bromopyruvate and 7 ml of dimethylformamide was stirred at 80° C. for 30 min. After cooling the precipitated crystals were filtered off, washed with ethanol and dried to yield 0.41 g (85%) of the title compound; Mp.: 242-243° C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858605B2uspto-grants-2005_02