Water → 2,3-Dichloro-N-methylmaleimide

HRID 741662ノート

反応式

HRID 741662 の反応式
[O-]CC.[Na+].[Cl:5][C:6]1[C:7]([O:9][C:10](=O)[C:11]=1[Cl:12])=[O:8].Cl.[CH3:15][NH2:16].O>C(O)(=O)C>[Cl:5][C:6]1[C:7]([N:16]([CH3:15])[C:10](=[O:9])[C:11]=1[Cl:12])=[O:8]

参加物

6

反応物 4

HCID 962WaterHCID 70728Dichloromaleic anhydrideHCID 2723922Sodium ethoxideHCID 6364545Methylamine hydrochloride

生成物 1

HCID 142932,3-Dichloro-N-methylmaleimide収率 64%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
25 °C

実験手順

Sodium ethoxide (3.56 g, 50 mmol) was added to a solution containing 2,3-dichloromaleic anhydride (5.56 g, 33.3 mmol) and methylamine hydrochloride (3.50 g, 55.0 mmol) in 40 mL of acetic acid. The mixture was stirred under a CaCl2 drying tube at 25° C. for 16 hours and then refluxed for 4 hours. The cooled mixture was poured into water (350 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 100 mL portions of saturated aqueous NaHCO3, water and brine and dried (MgSO4). The solvent was evaporated under reduced pressure. The residue was recrystallized from ethanol to give 3.82 g (64%) of 2,3-dichloro N-methylmaleimide as white crystals. Concentration of the mother liquor and chromatography of the residue by radial preparative layer chromatography (Chromatotron, Harrison Research), gave an additional 0.81 g of 2,3-dichloro N-methylmaleimide, raising the yield to 77%.

後処理

  1. temperaturerefluxed for 4 hours
  2. extractionextracted with EtOAc (3×75 mL)
  3. washThe combined organic extracts were washed with 100 mL portions of saturated aqueous NaHCO3, water and brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-f90daaebffd34fd5b84fded4b6c2ea5a
出典データセット
uspto-grants-1996_09
特許番号
US05552396

反応ノート

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