Water → N-2-(2-Furanyl)propenylphthalimide

HRID 256381

反応式

HRID 256381 の反応式
ClN1[C:6](=O)[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([Se][Se]C2C=CC=CC=2)[CH:14]=CC=C[CH:10]=1.[C:23]1(=[O:33])[NH:27][C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K].O>CN(C=O)C>[O:8]1[CH:3]=[CH:4][CH:5]=[C:6]1[C:9]([CH3:14])=[CH:10][N:27]1[C:23](=[O:33])[C:24]2=[CH:32][CH:31]=[CH:30][CH:29]=[C:25]2[C:26]1=[O:28]

参加物

6

反応物 4

HCID 962WaterHCID 15460Diphenyl diselenideHCID 31398ChlorosuccinimideHCID 24194345Phthalimide potassium salt

生成物 1

HCID 53798517N-2-(2-Furanyl)propenylphthalimide収率 299.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of 8.35 g (0.077 mole) of the olefin of Step A in 310 ml of DMF was added 12.37 g (0.093 mole) of N-chlorosuccinimide and 1.46 g (0.0047 mole) of diphenyl diselenide. After 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3. The hexane was distilled off at atmospheric pressure and the residue was dissolved in 200 ml of DMF, 9.49 g (0.051 mole) of potassium phthalimide was added and the mixture was warmed to 90° C. under N2. After 45 min. the cooled reaction mixture was poured into water and the precipitated product was filtered off and recrystallized from ethylacetate/2-propanol, affording 3.57 g colorless crystals, mp. 136°-137° C.

後処理

  1. customAfter 3 hours at room temperature the mixture was partitioned between 500 ml of hexane and 1000 ml of 5% Na2S2O3
  2. distillationThe hexane was distilled off at atmospheric pressure
  3. dissolutionthe residue was dissolved in 200 ml of DMF
  4. customAfter 45 min. the cooled reaction mixture
  5. filtrationthe precipitated product was filtered off
  6. customrecrystallized from ethylacetate/2-propanol

出典と根拠

ORDレコード
ord-7c326113c7934c3eaca585bb14d50dfc
出典データセット
uspto-grants-1987_10
特許番号
US04703058

関連ノート

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