Propylene Glycol → Phthalimide

HRID 1603963Notes

Reaction equation

HRID 1603963 reaction equation
NC1C=C[C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=CC=1.C([N:16](CC)CC)C.CN(C1C=CC=CN=1)C.[CH2:30]([OH:34])[CH:31](O)[CH3:32]>O>[C:30]1(=[O:34])[NH:16][C:11](=[O:13])[C:10]2=[CH:9][CH:8]=[CH:5][CH:32]=[C:31]12

Participants

6

Reactant 4

HCID 1030Propylene GlycolHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 270494-(4-Aminophenyl)butanoic acid

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 2.40 g (16.3 mmol) and 2.80 g (15.6 mmol) of 4-(4aminophenyl)butyric acid in 20 mL of propylene glycol, 2.40 mL (1.74 g, 17.3 mmol) of triethylamine and 10 mg (0.08 mmol) of dimethylaminopyridine was heated to 140° C. The mixture became a clear solution after 5 min at 140° C. After stirring for 330 min, the reaction mixture was cooled to 25° C. and diluted with 20 mL of water. The solid phthalimide which had formed was filtered off. The filtrate was acidified with 3% HCl solution. The resulting solid was filtered off and was recrystallized from 2-propanol and water to give 0.62 g of compound 133 as a tan solid.

Workup

  1. customafter 5 min
  2. customat 140° C
  3. temperaturethe reaction mixture was cooled to 25° C.

Sources & evidence

ORD record
ord-48565e21718e40dba5f5630773535c44
Source dataset
uspto-grants-1999_11
Patent number
US05990166

Reaction notes

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