Tetrahydrophthalic anhydride → HCID 12881900, compound

HRID 344592

Reaction equation

HRID 344592 reaction equation
[CH2:1]1[CH:6]2[C:7]([O:9][C:10](=[O:11])[CH:5]2[CH2:4][CH:3]=[CH:2]1)=O.[CH2:12]([O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[Cl:23])[NH2:19])[CH:13]=[CH2:14]>C(O)(=O)C>[CH2:12]([O:15][C:16]1[CH:17]=[C:18]([N:19]2[C:10](=[O:11])[C:5]3[CH2:4][CH2:3][CH2:2][CH2:1][C:6]=3[C:7]2=[O:9])[CH:20]=[CH:21][C:22]=1[Cl:23])[CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 6810Tetrahydrophthalic anhydrideHCID 544961134-Chloro-3-[(prop-2-en-1-yl)oxy]aniline

Product 1

HCID 12881900HCID 12881900, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4.4 g of THPA, 5.3 g of 3B and 60 mL of glacial acetic acid was refluxed for 1 hour, then poured into 300 mL of ice water. The resulting mixture was allowed to stand for 10 minutes, then filtered. The collected solid was washed with cold water, dried under reduced pressure and recrystallized from ethyl acetate/hexane, to give N-(3-(allyloxy)-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimide (3C), as yellow crystals, m.p.: 118.5°-120° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationfiltered
  3. washThe collected solid was washed with cold water
  4. customdried under reduced pressure
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-93160ebf2a4a4814a78be9c823f58fad
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Linked notes

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