p-Toluenesulfonic acid → HCID 22025475, compound

HRID 733279Notes

Reaction equation

HRID 733279 reaction equation
[CH3:1][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>[CH2:13]([N:17]1[C:9](=[O:10])[C:4]2=[CH:3][C:2]([CH3:1])=[CH:12][CH:11]=[C:5]2[C:6]1=[O:8])[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 880694-Methylphthalic anhydride

Product 1

HCID 22025475HCID 22025475, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

N-Isobutyl-4-methylphthalimide is prepared as described in Example 2, starting with 6.0 g of 4-methylphthalic anhydride, 3.7 cm3 of isobutylamine and a catalytic amount of para-toluenesulphonic acid in 60 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for three hours and is then cooled to a temperature in the region of 20° C. The reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue is taken up in 50 cm3 of saturated aqueous sodium bicarbonate solution, and the mixture is then extracted twice with 75 cm3 of dichloromethane. The organic extracts are combined, dried over sodium sulphate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C., giving 6.7 g of N-isobutyl-4-methylphthalimide in the form of a white solid melting at 102° C.

Workup

  1. customN-Isobutyl-4-methylphthalimide is prepared
  2. temperatureis then cooled to a temperature in the region of 20° C
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  4. extractionthe mixture is then extracted twice with 75 cm3 of dichloromethane
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C.

Sources & evidence

ORD record
ord-d4e9599c8a194a6e9b6898fc098798c1
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

Loading…