2-Methoxyethane-1-sulfonyl chloride → HCID 86594616、化合物

HRID 225388ノート

反応式

HRID 225388 の反応式
[CH2:1]([N:8]1[CH2:15][CH2:14][C:13]2([C:17]3[CH:18]=[C:19]([NH2:23])[CH:20]=[CH:21][CH:22]=3)[CH2:16][CH:9]1[CH2:10][CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:15][CH2:14][C:13]2([C:17]3[CH:18]=[C:19]([NH:23][S:28]([CH2:27][CH2:26][O:25][CH3:24])(=[O:30])=[O:29])[CH:20]=[CH:21][CH:22]=3)[CH2:16][CH:9]1[CH2:10][CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 2

HCID 134802212-Methoxyethane-1-sulfonyl chlorideHCID 22064584HCID 22064584、化合物

生成物 1

HCID 86594616HCID 86594616、化合物

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 1140Toluene溶媒

実験手順

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-phenylamine (2.71 g, 8.84 mmol) stirred in pyridine (25 ml) at 0° C. was charged with 2-methoxy-ethanesulfonyl chloride (2.1 g, 13.26 mmol) dropwise causing a color change from yellow to bright orange. The reaction was allowed to warm to room temperature gradually and stirred 18 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with CH2Cl2 (2×50 ml) and the organic layer was concentrated to an oil. This was dissolved in EtOAc which caused an oil to separate. The EtOAc layer was separated and washed with saturated aqueous NaHCO3 solution (100 mL). The aqueous layer was extracted with EtOAc (2×50 ml) and the combined organic layer was washed with saturated aqueous NaCl solution (50 ml), dried over Na2SO4, filtered and concentrated to a crude orange liquid (3.77 g, ˜100%). (TLC 75% EtOAc/hexanes Rf 0.48);

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3 solution (100 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×50 ml)
  5. concentrationthe organic layer was concentrated to an oil
  6. dissolutionThis was dissolved in EtOAc which
  7. customto separate
  8. customThe EtOAc layer was separated
  9. washwashed with saturated aqueous NaHCO3 solution (100 mL)
  10. extractionThe aqueous layer was extracted with EtOAc (2×50 ml)
  11. washthe combined organic layer was washed with saturated aqueous NaCl solution (50 ml)
  12. dry with materialdried over Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated to a crude orange liquid (3.77 g, ˜100%)

出典と根拠

ORDレコード
ord-d2de0c9643b54223baee8050e9ef6cc5
出典データセット
uspto-grants-2009_07
特許番号
USRE040838E1

反応ノート

読み込み中…