Sodium Iodide → 1-Thioacetylmethyl-2-nitroimidazole

HRID 1875460

反応式

HRID 1875460 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 866562691-Thioacetylmethyl-2-nitroimidazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

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.

後処理

  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

出典と根拠

ORDレコード
ord-8296122d7f0340a3a24c6d0c5a488814
出典データセット
uspto-grants-2012_11
特許番号
US08309554B2

関連ノート

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