p-Toluenesulfonic acid → HCID 4126466, compound

HRID 733234Notes

Reaction equation

HRID 733234 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=O)[C:5]2=[CH:11][CH:12]=1.[CH2:13]([NH2:17])[CH:14]([CH3:16])[CH3:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[N:17]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6](=[O:8])[C:5]2=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 670444-Chlorophthalic anhydride

Product 1

HCID 4126466HCID 4126466, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

4-Chloro-N-isobutylphthalimide is prepared as described in Example 2, starting with 10 g of 4-chlorophthalic anhydride, 5.4 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 100 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 16 hours and is then cooled to a temperature in the region of 20° C. The reaction mixture is taken up in 100 cm3 of saturated aqueous sodium bicarbonate solution and the aqueous phase is extracted twice with 100 cm3 of ethyl acetate. The organic extracts are combined, washed with 50 cm3 of brine, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C. 12 g of 4-chloro-N-isobutylphthalimide are thus obtained in the form of a white powder. (Rf=0.85, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (75/25 by volume)).

Workup

  1. custom4-Chloro-N-isobutylphthalimide is prepared
  2. temperatureis then cooled to a temperature in the region of 20° C
  3. extractionthe aqueous phase is extracted twice with 100 cm3 of ethyl acetate
  4. washwashed with 50 cm3 of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  8. customThe residue is dried in a desiccator under reduced pressure (2 kPa) at a temperature in the region of 20° C

Sources & evidence

ORD record
ord-eafd6003e1bd4126a373cf9299b4c1c5
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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