Reaktion #1962642

Reaktionsgleichung

chloromethylthioacetate

2-nitroimidazole

NaI

diisopropylethyl amine

DIEA

→

1-thioacetylmethyl-2-nitroimidazole

Lösungsmittel

MeCN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturrefluxed
2. 2
   SonstigeA precipitate formed after 3 h
3. 3
   Temperaturrefluxed for 4 h
4. 4
   SonstigeVolatiles were removed
5. 5
   workup.ADDITIONEtOAc (300 mL) added to the residue
6. 6
   Filtrationthe ensuing mixture filtered
7. 7
   WaschenThe filtrate was washed with water, 1M aqueous citric acid, brine
8. 8
   Einengenconcentrated
9. 9
   Sonstigeto yield a residue
10. 10
    SonstigeThe residue was separated by column chromatography

Vorschrift

To a solution of the chloromethylthioacetate in MeCN (100 mL) was added 2-nitroimidazole (3 g), NaI (1 g) and diisopropylethyl amine (DIEA) and refluxed. A precipitate formed after 3 h. Additional DIEA (3 mL) was added to the reaction mixture and refluxed for 4 h. Volatiles were removed, EtOAc (300 mL) added to the residue, and the ensuing mixture filtered. The filtrate was washed with water, 1M aqueous citric acid, brine, and concentrated to yield a residue. The residue was separated by column chromatography using 0-90% EtOAc/Hexane as eluent to yield 1-thioacetylmethyl-2-nitroimidazole (vi, 3.15 g) that was chlorinated as described above in Example 1A to yield compound vii.

Quelle