Phosphorus pentachloride → (4-Nitrophthalimido)acetyl chloride

HRID 1198950Notes

Reaction equation

HRID 1198950 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][C:14](O)=[O:15])[C:8](=[O:9])[C:7]2=[CH:17][CH:18]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:10]([CH2:13][C:14]([Cl:20])=[O:15])[C:8](=[O:9])[C:7]2=[CH:17][CH:18]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 2727372-(5-nitro-1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid

Product 1

HCID 15100608(4-Nitrophthalimido)acetyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 2-(4-nitrophthalimido)acetic acid (58.6 g) in toluene (250 ml) was added phosphorus pentachloride (48.8 g) and the mixture was refluxed for 3 hours. After completion of the reaction, the solvent was removed under reduced pressure. By addition of hexane to the residue, the title compound (62.3 g) was obtained as light yellow sharp-pointed needles.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed under reduced pressure
  4. additionBy addition of hexane to the residue

Sources & evidence

ORD record
ord-c117ea93444b4ec7b7aa2202c7d355e7
Source dataset
uspto-grants-1990_02
Patent number
US04898859

Reaction notes

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