Sodium Carbonate → HCID 57468838、化合物

HRID 1989260ノート

反応式

HRID 1989260 の反応式
Cl.[CH3:2][O:3][NH2:4].C([O-])([O-])=O.[Na+].[Na+].[Br:11][C:12]1[CH:13]=[C:14]([S:18](Cl)(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1.[OH-].[Na+]>C1COCC1.O.O1CCOCC1>[Br:11][C:12]1[CH:13]=[C:14]([S:18]([NH:4][O:3][CH3:2])(=[O:20])=[O:19])[CH:15]=[CH:16][CH:17]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 17943m-Bromobenzenesulphonyl chlorideHCID 521874O-Methylhydroxylamine hydrochloride

生成物 1

HCID 57468838HCID 57468838、化合物収率 50%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
23 °C

実験手順

To a solution of commercially available methoxyamine hydrochloride (1.96 g, 23.4 mmol) and 2 M Na2CO3-solution (20 mL, 40 mmol) in THF (100 mL) at 0° C. was added dropwise added commercially available 3-bromobenzenesulfonyl chloride (2.5 g, 9.8 mmol) and the mixture was stirred at 23° C. for 18 h. The reaction is diluted with water, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated to give a light brown solid, which was refluxed with 1 M NaOH (10 mL) in dioxane (10 mL) for 30 min to cleave disulfonylated product. Cooled to rt, diluted with water, extracted with EtOAc, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left a light brown solid, which was purified by trituration with heptane/diethyl ether gave the title compound as a light yellow solid (1.30 g, 50%). MS (ISN) 264.0 [(M−H)−] and 266.0 [(M+2−H)−].

後処理

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a light brown solid, which
  7. temperatureCooled to rt
  8. extractionextracted with EtOAc
  9. washwashed organic layer with brine
  10. dry with materialdried over Na2SO4
  11. customRemoval of the solvent in vacuum
  12. waitleft a light brown solid, which
  13. customwas purified by trituration with heptane/diethyl ether

出典と根拠

ORDレコード
ord-ee74bc9523844f7bb385455e6152c11c
出典データセット
uspto-grants-2010_01
特許番号
US07642264B2

反応ノート

読み込み中…