Sodium Iodide → 1-Thioacetylmethyl-2-nitroimidazole

HRID 1875460

Reaction equation

HRID 1875460 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 866562691-Thioacetylmethyl-2-nitroimidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8296122d7f0340a3a24c6d0c5a488814
Source dataset
uspto-grants-2012_11
Patent number
US08309554B2

Linked notes

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