反応 #1962642

反応方程式

chloromethylthioacetate

2-nitroimidazole

NaI

diisopropylethyl amine

DIEA

→

1-thioacetylmethyl-2-nitroimidazole

溶媒

MeCN

反応条件

後処理

1. 1
   温度refluxed
2. 2
   その他A precipitate formed after 3 h
3. 3
   温度refluxed for 4 h
4. 4
   その他Volatiles were removed
5. 5
   workup.ADDITIONEtOAc (300 mL) added to the residue
6. 6
   ろ過the ensuing mixture filtered
7. 7
   洗浄The filtrate was washed with water, 1M aqueous citric acid, brine
8. 8
   濃縮concentrated
9. 9
   その他to yield a residue
10. 10
    その他The residue was separated by column chromatography

実験手順

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.

出典