Hexamethylenetetramine → N-(3-formyl-4-methoxybenzyl)phthalimide

HRID 47298Notes

Reaction equation

HRID 47298 reaction equation
C1N2CN3CN(C2)CN1C3.[CH3:11][O:12][C:13]1[CH:30]=[CH:29][C:16]([CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[CH:15][CH:14]=1.FC(F)(F)[C:33](O)=[O:34].C(=O)([O-])[O-].[K+].[K+]>O>[CH:33]([C:30]1[CH:29]=[C:16]([CH:15]=[CH:14][C:13]=1[O:12][CH3:11])[CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])=[O:34]

Participants

6

Reactant 4

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 519849HCID 519849, compound

Product 1

HCID 22744477N-(3-formyl-4-methoxybenzyl)phthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18 g of hexamethylene tetramine was added little by little to a mixture of 31 g N-(4-methoxybenzyl)phthalimide and 100 ml trifluoroacetic acid, stirred at room temperature for 1 hr, and then heated under reflux for 4 hr. The reaction solution was cooled to 0° C., and water was added thereto. Potassium carbonate was added thereto and the resulting crystals were collected by filtration. The crystals were dried to give 20 g of N-(3-formyl-4-methoxybenzyl)phthalimide.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 hr
  3. temperatureThe reaction solution was cooled to 0° C.
  4. filtrationthe resulting crystals were collected by filtration
  5. customThe crystals were dried

Sources & evidence

ORD record
ord-eee8f82877534586b2e13c04077af236
Source dataset
uspto-grants-2004_03
Patent number
US06699870B2

Reaction notes

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