Propargyl bromide → HCID 15007143, compound

HRID 1086995Notes

Reaction equation

HRID 1086995 reaction equation
[O:1]=[C:2]1[CH2:6][S:5][CH2:4][NH:3]1.[H-].[Na+].[CH2:9](Br)[C:10]#[CH:11].C(=O)(O)[O-].[Na+]>CN(C)C=O.C1(C)C=CC=CC=1>[CH2:11]([N:3]1[C:2](=[O:1])[CH2:6][S:5][CH2:4]1)[C:10]#[CH:9]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 6375914-Thiazolidinone

Product 1

HCID 15007143HCID 15007143, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 10.3 g of 4-oxothiazolidine in 500 ml of anhydrous dimethylformamide under N2 was added 6.0 g of sodium hydride (50% in oil). After 30 min., 15 ml of a solution of 80% propargyl bromide in toluene was added and the mixture was allowed to stir for another hour. The mixture was then poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic fractions were washed twice with water, then once with brine, dried (MgSO4), filtered and concentrated. The residue was distilled at 0.1/mm Hg, 95°-98° C., to provide 9.248 g of 3-propargyl-4-oxothiazolidine as an oil which solidified upon refrigeration, mp 29°-31°.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic fractions were washed twice with water
  3. dry with materialonce with brine, dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. distillationThe residue was distilled at 0.1/mm Hg, 95°-98° C.

Sources & evidence

ORD record
ord-7468f7d168c74f7589e5df81e6b9e5f9
Source dataset
uspto-grants-1991_07
Patent number
US05034392

Reaction notes

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