Water → HCID 51190539, compound

HRID 346237Notes

Reaction equation

HRID 346237 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][O:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25]Cl)=[C:18](C)[CH:17]=1.O.CN(C)[CH:32]=[O:33]>>[CH3:13][O:14][C:15](=[O:28])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])=[C:18]([O:33][CH3:32])[CH:17]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 54529805HCID 54529805, compound

Product 1

HCID 51190539HCID 51190539, compoundYield 80%

Procedure

A mixture of 66.9 g (0.354 mole) of potassium phthalimide (98%, Aldrich) and 90.0 g (0.348 mole) of 4-(3-chloropropoxy)-3-methyl benzoic acid methyl ester in 450 mL of dimethyl formamide was stirred and heated at reflux for 5 hr then let stir at ambient temperature overnight. The reaction mixture was treated with 3 L of water and the resulting solid was collected by filtration to give 108.5 g (84%) of crude title compound. An 8.0 g sample of this solid was recrystallized from 2-propanol to yield 6.4 g (80%) of title compound as a white solid, mp 127°-128° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hr
  3. stirringthen let stir at ambient temperature overnight
  4. filtrationthe resulting solid was collected by filtration
  5. customto give 108.5 g (84%) of crude title compound
  6. customAn 8.0 g sample of this solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-5c36402a52d649d1abbbfde2214b72e5
Source dataset
uspto-grants-1991_10
Patent number
US05061720

Reaction notes

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