Water → 2,3-Dichloro-N-methylmaleimide

HRID 741662

반응식

HRID 741662 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 142932,3-Dichloro-N-methylmaleimide수율 64%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
25 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-f90daaebffd34fd5b84fded4b6c2ea5a
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05552396

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