p-Toluenesulfonic acid → HCID 22025412, compound

HRID 733266Notes

Reaction equation

HRID 733266 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([NH:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[O:12])[C:5](=[CH:9][CH:10]=1)[C:6](O)=[O:7].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:11](=[O:12])[N:13]([CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])[C:6](=[O:7])[C:5]2=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22025467HCID 22025467, compound

Product 1

HCID 22025412HCID 22025412, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5.0 g of 4-chloro-N-(3,3,3-trifluoropropyl)phthalamic acid and 30 mg of para-toluenesulfonic acid in 100 cm3 of toluene is refluxed with stirring for 7 hours. The reaction mixture is then concentrated to dryness under reduced pressure. 4.2 g of 4-chloro-N-(3,3,3-trifluoropropyl)phthalimide are thus obtained, Rf=0.5 (thin layer chromatography on silica gel, eluent: diisopropyl ether. Mass spectrum: DCI: m/e 278.

Workup

  1. temperatureis refluxed
  2. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-93db3ad2fb6742ff95949a709a5ee90d
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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