NSC260518 → HCID 14713891, compound

HRID 1649986Notes

Reaction equation

HRID 1649986 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].CS(O[CH2:18][CH:19]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH3:20])(=O)=O>CN(C)C=O>[CH3:25][S:22]([O:21][CH:19]([CH3:20])[CH2:18][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])(=[O:24])=[O:23]

Participants

4

Reactant 2

HCID 319059NSC260518HCID 24194345Phthalimide potassium salt

Product 1

HCID 14713891HCID 14713891, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.55 g (30 mmoles) of potassium phthalimide are added in small portions, within 1 hour, to a solution of 7.0 g (30 mmoles) of 1,2-bis(methanesulfonyloxy)-propane in 70 ml of dry dimethyl formamide, heated to 100°-105° C. The mixture is stirred at the same temperature for additional 0.5 hours, thereafter it is cooled and poured onto 350 ml of ice water. The separated crystalline substance is filtered off, washed with water and dried. This crude product, weighing 4.36 g (m.p.: 111°-121° C.) is recrystallized from 25 ml of isopropanol to obtain 3.53 g (41.5%) of N-(β-methanesulfonyloxy-propyl)-phthalimide; m.p.: 129°-132° C.

Workup

  1. temperatureheated to 100°-105° C
  2. temperatureit is cooled
  3. filtrationThe separated crystalline substance is filtered off
  4. washwashed with water
  5. customdried
  6. customis recrystallized from 25 ml of isopropanol

Sources & evidence

ORD record
ord-683a82a1b681463dad0004b83275a93c
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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