Pyridine → 1-{2-(2-Fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

HRID 1747354ノート

反応式

HRID 1747354 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]([CH3:21])=[CH2:20])[C:11]1=[O:22].Cl.[NH2:25][OH:26].N1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:25][OH:26])[CH2:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([C:19]([CH3:21])=[CH2:20])[C:11]1=[O:22]

参加物

5

反応物 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 594974541-[2-(2-Fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

生成物 1

HCID 723080691-{2-(2-Fluoro-phenyl)-2-[hydroxyimino]-ethyl}-3-isopropenyl-1,3-dihydro-benzimidazol-2-one収率 73.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 1-[2-(2-fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one (1.3 g, 4.2 mmol) in ethanol (50 ml) was added hydroxylamine hydrochloride (0.84 g, 12.2 mmol) followed by pyridine (1.7 ml, 21.0 mmol) at ambient temperature. The resulting mixture was warmed to 80° C. for 6 h, cooled to ambient temperature and concentrated. The remaining residue was diluted with water, 1M HCl and ethyl acetate. The layers were separated and the aqueous phase was extracted once more with ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated to give the crude product which was purified via column chromatography (silica gel, 50% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 1.0 g (73%) of the desired product as an oil which solidified on standing.

後処理

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated
  3. additionThe remaining residue was diluted with water, 1M HCl and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted once more with ethyl acetate
  6. dry with materialThe combined organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product which
  10. customwas purified via column chromatography (silica gel, 50% EtOAc/hexanes)
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-3d71513c1a2c4c63b6c17463a7c809b7
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

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