Sodium Iodide → 1-Thioacetylmethyl-2-nitroimidazole

HRID 1875460

Reaktionsgleichung

Reaktionsgleichung von HRID 1875460
ClCO[C:4](=[S:6])[CH3:5].[N+:7]([C:10]1[NH:11][CH:12]=[CH:13][N:14]=1)([O-:9])=[O:8].[Na+].[I-].[CH:17](N(C(C)C)CC)(C)C>CC#N>[C:4]([CH2:17][N:11]1[CH:12]=[CH:13][N:14]=[C:10]1[N+:7]([O-:9])=[O:8])(=[S:6])[CH3:5]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 107012-NitroimidazoleHCID 81531Diisopropylethylamine2×HCID 53833355Chloromethylthioacetate

Produkt 1

HCID 866562691-Thioacetylmethyl-2-nitroimidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperaturerefluxed
  2. customA precipitate formed after 3 h
  3. temperaturerefluxed for 4 h
  4. customVolatiles were removed
  5. additionEtOAc (300 mL) added to the residue
  6. filtrationthe ensuing mixture filtered
  7. washThe filtrate was washed with water, 1M aqueous citric acid, brine
  8. concentrationconcentrated
  9. customto yield a residue
  10. customThe residue was separated by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8296122d7f0340a3a24c6d0c5a488814
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309554B2

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