Potassium Iodide → HCID 13674821, compound

HRID 1649983Notes

Reaction equation

HRID 1649983 reaction equation
Cl[CH2:2][CH:3]([N:5]([C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17])[S:6]([CH3:9])(=[O:8])=[O:7])[CH3:4].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].[I-].[K+]>CN(C)C=O>[C:18]1(=[O:28])[N:22]([CH2:2][CH:3]([N:5]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[S:6]([CH3:9])(=[O:8])=[O:7])[CH3:4])[C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 13674816HCID 13674816, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 13674821HCID 13674821, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

45.3 g (0.164 moles) of 1-chloro-2-[N-(2,6-dimethylphenyl)-methanesulfonamido]-propane are dissolved in 700 ml of dry dimethyl formamide, 61 g (0.33 moles) of potassium phthalimide and 1 g (6 mmoles) of potassium iodide are added, and the mixture is stirred at 140°-145° C. for 7 hours. The reaction mixture is processed as described in Example 21 for the preparation of the starting substance. The resulting 46.6 g of crude, honey-like substance is triturated with 50 ml of diethyl ether, the separated crystalline substance is filtered off, washed with diethyl ether and dried. 23.05 g of a crystalline substance are obtained; m.p.: 155°-160° C. This substance is purified further by stirring it with 50 ml of diethyl ether at room temperature. Thereafter the crystals are filtered off, washed with diethyl ether and dried. 16.75 g (26.4%) of 1-phthalimido-2-[N-(2,6-dimethylphenyl)-methanesulfonamido]-propane are obtained; m.p.: 188°-190° C.

Workup

  1. customas described in Example 21 for the preparation of the starting substance
  2. customThe resulting 46.6 g of crude, honey-like substance is triturated with 50 ml of diethyl ether
  3. filtrationthe separated crystalline substance is filtered off
  4. washwashed with diethyl ether
  5. customdried
  6. custom23.05 g of a crystalline substance are obtained
  7. customThis substance is purified further
  8. stirringby stirring it with 50 ml of diethyl ether at room temperature
  9. filtrationThereafter the crystals are filtered off
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-3f93970f8dd84cb881519d660fb254e9
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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