1,4-Dichloro-2-butene, (2E)- → 2-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dione

HRID 1698876

Reaction equation

HRID 1698876 reaction equation
[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5]Cl.[C:7]1(=[O:17])[NH:11][C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]12.[K]>>[Cl:1][CH2:2]/[CH:3]=[CH:4]/[CH2:5][N:11]1[C:10](=[O:12])[C:9]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:8]2[C:7]1=[O:17]

Participants

3

Reactant 2

HCID 6421971,4-Dichloro-2-butene, (2E)-HCID 24194345Phthalimide potassium salt

Product 1

HCID 57093742-((2E)-4-chlorobut-2-en-1-yl)-2,3-dihydro-1H-isoindole-1,3-dioneYield 61%

Conditions

Temperature
20 °C

Procedure

Ex-7a) Under argon, to 65.8 g of trans-1,4-dichloro-2-butene was added in portions 47 g of potassium phthalimide with mechanical stirring maintaining the temperature between 100° C. and 110° C. The reaction mixture was then stirred for 2 h keeping the temperature between 145° C. to 150° C. It was then cooled to 20° C. and extracted with 3×400 mL of ether. The ether layer was separated and stripped to give a solid. This solid was recrystallized from ethanol to yield yellow crystals of N-(trans-4-Chloro-2-butenyl)phthalimide, wt. 36 g, 61% yield. Analysis calcd. for C12H10ClNO2 (MW 237.25): C, 61.26; H, 4.29; N, 6.02; Cl, 14.94; Found C, 61.18; H, 4.30; N, 5.98; Cl, 14.62.

Workup

  1. temperaturemaintaining the temperature between 100° C. and 110° C
  2. stirringThe reaction mixture was then stirred for 2 h
  3. custombetween 145° C. to 150° C
  4. extractionextracted with 3×400 mL of ether
  5. customThe ether layer was separated
  6. customto give a solid
  7. customThis solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-3c564d79c5ac4235b304cbac305ebdb1
Source dataset
uspto-grants-2002_02
Patent number
US06344483B1

Linked notes

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