HCID 13674813, compound → HCID 13674820, compound

HRID 1649981Notes

Reaction equation

HRID 1649981 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][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[N:21]([CH2:26][CH:27](OS(C)(=O)=O)[CH3:28])[S:22]([CH3:25])(=[O:24])=[O:23]>CN(C)C=O>[CH3:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:15]=1[N:21]([CH2:26][CH:27]([N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6])[CH3:28])[S:22]([CH3:25])(=[O:23])=[O:24]

Participants

4

Reactant 2

HCID 13674813HCID 13674813, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 13674820HCID 13674820, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33.3 g/0.19 moles of potassium phthalimide are added to a solution of 30 g (89 mmoles) of 1-[N-(2,6-dimethylphenyl)-methane-sulfonamido]-2-methanesulfonyloxy-propane in 300 ml of dry dimethyl formamide, and the mixture is stirred at 145°-150° C. for one hour. The mixture is cooled, poured onto 800 ml of ice water, and the aqueous mixture is extracted thrice with 200 ml of chloroform, each. The chloroform solution is washed thrice with 50 ml of n sodium hydroxide solution and then thrice with 100 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. The oily residue is triturated with 35 ml of isopropanol, the separated crystalline substance is filtered off, washed with ice-cold isopropanol and dried. 22 g (64.1%) of 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-2-phthalimido-propane are obtained as a colourless, crystalline substance; m.p.: 124°-127° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionthe aqueous mixture is extracted thrice with 200 ml of chloroform
  3. washThe chloroform solution is washed thrice with 50 ml of n sodium hydroxide solution
  4. dry with materialeach, dried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe oily residue is triturated with 35 ml of isopropanol
  7. filtrationthe separated crystalline substance is filtered off
  8. washwashed with ice-cold isopropanol
  9. customdried

Sources & evidence

ORD record
ord-2d2e6996ea2f4306a6975071203b08d4
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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