Water → N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 21478

반응식

HRID 21478 반응식
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[NH2:4].[C:15]1(=O)[O:20][C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]1=2.O>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([O:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][C:3]=1[N:4]1[C:18](=[O:19])[C:17]2[CH2:21][CH2:22][CH2:23][CH2:24][C:16]=2[C:15]1=[O:20]

참가 물질

5

반응물 3

HCID 962WaterHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 107989305-Amino-2-chloro-4-fluorophenyl methyl carbonate

생성물 1

HCID 19374481N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide수율 79.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 2-fluoro-4-chloro-5-methoxycarbonyloxyaniline (20.0 g, 91.1 mmol) and 3,4,5,6-tetrahydrophthalic anhydride (14.0 g, 92.0 mmol) in acetic acid (200 ml) was reacted for 5 hours while heating under refluxing. After completion of the reaction, the mixture was-cooled to room temperature, water (200 ml) was added thereto, and extracted with ethyl acetate (100 ml×3 times). The organic layer was washed with an aqueous solution of sodium carbonate and water, dried, and the solvent was distilled off under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5) to obtain N-(2-fluoro-4-chloro-5-methoxycarbonyloxyphenyl)-3,4,5,6-tetrahydrophthalimide as a white solid (26.2 g, 72.1 mmol, 79.2% yield).

후처리

  1. temperaturewhile heating
  2. temperatureunder refluxing
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate (100 ml×3 times)
  5. washThe organic layer was washed with an aqueous solution of sodium carbonate and water
  6. customdried
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting oily substance was purified by silica gel column chromatography (development solvent: ethyl acetate/hexane=1/5)

출처 및 근거

ORD 기록
ord-09cb1a08229048beaa4bbad76741f767
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424277

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