Phthalic Anhydride → HCID 53649200, compound

HRID 344609Notes

Reaction equation

HRID 344609 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[NH2:8])[CH:2]=[CH2:3].[C:14]1(=O)[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([N:8]2[C:17](=[O:18])[C:16]3=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]3[C:14]2=[O:19])[C:9]([F:13])=[CH:10][C:11]=1[Cl:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 132729265-Allyloxy-4-chloro-2-fluoroaniline

Product 1

HCID 53649200HCID 53649200, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 20.2 g of 19A and 14.8 g of phthalic anhydride in 300 mL of toluene was treated with 1.01 g of triethylamine and heated to reflux for 16 hours with a Dean-stark trap to effect azeotropic removal of water. The toluene was removed in vacuo, the residue was dissolved in 800 mL of methylene chloride, and treated with 35 g charcoal. After filtration through celite and concentration of solvent in vacuo, the residue was recrystallized from ethanol to afford N-[3-(allyloxy)-4-chloro-6-fluorophenyl]phthalimide (41A) as tan crystals, m.p.: 148°-150° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 hours with a Dean-stark trap
  3. customremoval of water
  4. customThe toluene was removed in vacuo
  5. dissolutionthe residue was dissolved in 800 mL of methylene chloride
  6. additiontreated with 35 g charcoal
  7. filtrationAfter filtration through celite and concentration of solvent in vacuo
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-2d08cf458c1247ed8346f5e1f2c47d4f
Source dataset
uspto-grants-1991_10
Patent number
US05053071

Reaction notes

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