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

HRID 21478

反応式

HRID 21478 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-09cb1a08229048beaa4bbad76741f767
出典データセット
uspto-grants-1995_06
特許番号
US05424277

関連ノート

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