Dimethyl Sulfoxide → 4-(p-chlorophenyl)-N-methyl phthalimide

HRID 1731879Notes

Reaction equation

HRID 1731879 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.CS(C)=O.[OH-].[Na+].[N+]([C:18]1[CH:19]=[C:20]2[C:25](=[O:26])[N:24]([CH3:27])[C:22](=[O:23])[C:21]2=[CH:28][CH:29]=1)([O-])=O>O.ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[CH:19]=[C:20]3[C:25](=[O:26])[N:24]([CH3:27])[C:22](=[O:23])[C:21]3=[CH:28][CH:29]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 923214-Nitro-N-methylphthalimide

Product 1

HCID 201956994-(p-chlorophenyl)-N-methyl phthalimideYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7964ChlorobenzeneSolvent

Procedure

In a 500 ml three-necked flask equipped with a mechanical stirrer, Dean-Stark trap/condenser, nitrogen inlet, and thermometer was added 25.71 grams (0.20 moles) of p-chlorophenol, 100 ml dimethylsulfoxide, and 150 ml of chlorobenzene. After stirring and nitrogen purging the mixture for 30 min., 15.80 grams of aqueous sodium hydroxide (50.62 wt. %; 0.20 moles) was added. The mixture was heated up to 150° C. with the azeotropic removal of the water of reaction. After the removal of water was complete the temperature was lowered to 60° C. and 41.23 grams (0.20 moles) of 4-nitro-N-methyl phthalimide was added. The mixture was stirred overnight. Upon cooling to room temperature the product precipitated from solution. Filtration, washing the precipitate with water, and recrystallization from isopropanol yielded 50.8 grams of 4-(p-chlorophenyl)-N-methyl phthalimide. The melting point was 131°-132° C.

Workup

  1. customIn a 500 ml three-necked flask equipped with a mechanical stirrer
  2. customAfter the removal of water
  3. customwas lowered to 60° C.
  4. stirringThe mixture was stirred overnight
  5. customprecipitated from solution
  6. filtrationFiltration
  7. washwashing the precipitate
  8. customwith water, and recrystallization from isopropanol

Sources & evidence

ORD record
ord-2bd0b445152d4cf5a26964474a844ce0
Source dataset
uspto-grants-1986_11
Patent number
US04623732

Reaction notes

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