p-Toluenesulfonic acid → HCID 840420, compound

HRID 733238Notes

Reaction equation

HRID 733238 reaction equation
[Br: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>[Br: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

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6558IsobutylamineHCID 665904-Bromophthalic anhydride

Product 1

HCID 840420HCID 840420, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

4-Bromo-N-isobutylphthalimide is prepared as described in Example 2, starting with 20 g of 4-bromophthalic anhydride, 9.2 cm3 of isobutylamine and a catalytic amount of para-toluenesulfonic acid in 200 cm3 of toluene. The reaction mixture is heated at a temperature in the region of 140° C. for 6 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., and the residue is then taken up in 350 cm3 of ethyl acetate and 300 cm3 of saturated sodium hydrogen carbonate solution. The aqueous phase is separated out after settling has taken place and then extracted twice with 350 cm3 of ethyl acetate. The combined organic extracts are washed with 300 cm3 of saturated 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. 23.6 g of 4-bromo-N-isobutylphthalimide are thus obtained in the form of a white powder (Rf=0.91, thin layer chromatography on silica gel, eluent: cyclohexane/ethyl acetate (50/50 by volume)).

Workup

  1. custom4-Bromo-N-isobutylphthalimide 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. customThe aqueous phase is separated out after settling
  5. extractionextracted twice with 350 cm3 of ethyl acetate
  6. washThe combined organic extracts are washed with 300 cm3 of saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-815c64e065b349138d96639c1f945efb
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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