Sodium Iodide → 1-Thioacetylmethyl-2-nitroimidazole

HRID 1875460

반응식

HRID 1875460 반응식
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]

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 107012-NitroimidazoleHCID 81531Diisopropylethylamine2회HCID 53833355Chloromethylthioacetate

생성물 1

HCID 866562691-Thioacetylmethyl-2-nitroimidazole

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8296122d7f0340a3a24c6d0c5a488814
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309554B2

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